


Mistress wanted

by MadMax87 (Madmax87)



Category: Harry Potter - J. K. Rowling
Genre: Anal, Butt Plugs, Crossdressing, Cunnilingus, Femdom, Feminization, Humiliation, Masturbation, Multi, Panty Raid, Rimming, Sex Toys, Small Penis, Spitroasting, Strap-Ons, Watersports
Language: English
Status: In-Progress
Published: 2020-01-12
Updated: 2020-02-02
Packaged: 2021-02-27 08:54:14
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 8
Words: 25,176
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22224439
Author URL: https://archiveofourown.org/users/Madmax87/pseuds/MadMax87
Summary: Harry was alone and needed someone to help him find some direction.He might have bit off more then he could chew, but in the end, he couldn't complain. She was doing exactly what he wanted. Even if he didn't know that at the time.
Relationships: Cho Chang/Harry Potter
Comments: 35
Kudos: 148





	1. Chapter 1

**Author's Note:**

> I am in no way a proper author. I am writing this purely for the fact that I would myself love to read something like this. There aren't any that I can find, so I am sharing this instead. 
> 
> I have no beta so I'm sure there are alot of mistakes I might have missed. Feel free to point any annoying ones out to me.
> 
> Tags to be updated as i go

**Chapter one**  
 **How it began**  
It had been a year since the end of the war.  
Voldemort was dead, the Death eaters from the final battle were captured and imprisoned.  
The magical world of Britain had spent the year repairing the ministry, Hogwarts and relations with other countries.  
Everyone was happy and moving onto a new dawn without the bigotry and seclusion from the past.  
Everyone that is, except Harry Potter…….  
**********************************  
Harry Potter had lost a lot of people during the war, but he had somehow managed to survive.  
Ron and Hermione had started their relationship in earnest after the battle. Harry and Ginny didn’t. It only took her kissing him once after Fred’s funeral for him to realize that he didn’t feel anything for her any longer. It was the screeching she had done after he expressed his lack of feelings that caused him to retreat to muggle London and not look back.

There was a problem however.  
He had no idea what to do... Not just for a job, but for his life in general. He was never prepared for life after the battle. All he had known was Voldemort and the war. He felt like he was just floating along, he had no desire to study or find a job. His inheritance more than provided any money he required. Especially after the Goblins instructed him to remove everything from his vaults before banning him from any Gringotts bank worldwide. He moved himself into a spacious secluded home outside of London, with a large wood surrounding his property from his neighbors. It was previously owned by a grey magical family, so he had renewed the wards on the property preventing him from being found and then spent the next year slowly working on the gardens and repairing the house as he had been “taught” growing up with the Dursleys.  
It was shortly after the year mark that he had been living in isolation that he had realized that he needed something more than the life he was living. He had realized that what he really needed was a “Hermione”. Not the actual Hermione, just someone like her. He needed someone in his life that would help him out of his slump. He needed someone to tell him what to do…  
And that’s how it started…..

 **Advertisement**  
I require a live-in, female Mistress of the house to assist me in my affairs and organizing my plans for the future. I require someone strong willed and stern, but that can have fun. You should be single as I will require your full attention. You should be able to think independently and able to use your initiative as much as possible. Food and board will be provided as well as access to finances as required  
Please forward your references to the Post Mailbox below.

 **Meeting the candidate**  
Harry was sitting in the room waiting for the person to enter.  
He was wearing a long black hooded cloak, hiding his face from view. He was quite nervous, truth be told. He had started berating himself immediately after the owl had left with the advertisement to the Daily Prophet. He thought himself mad, but it was done. He couldn’t even figure out why he had written the advert as he had. He originally had set out to just advertise for a roommate that might be able to alleviate some loneliness. He honestly hadn’t expected any responses to the advert, and was surprised when he received only one.  
Which was why he was here.  
The only problem he had, was that the one response he had received had been as vague as his advert to begin with. There was no name attached and no indication as to who the person was other than the letter indicating that “she” matched the brief and would meet him at Three Broomsticks private room to discuss the specific requirements of the role.

It was during these ruminations that there was a sharp knock on the door and it opened before he could call out for the person to enter.  
The woman who entered was pretty average and nondescript. She was tell, average short brown hair, brown eyes and average figure. Probably about 30 years old.

She entered and took the seat across the table from him without saying a word. And then proceeded to stare at him for a minute.

It was starting to get a little uncomfortable when Harry finally broke the silence.  
“Good day Ma’am. I appreciate you meeting with me. I apologize for concealing myself, but I value my privacy and felt that it would be safer. You may call me James.”

The woman’s eyes seemed to widen only slightly at the greeting and settled just as quickly. She sat slightly taller and kept her hands casually on the table in front of her.  
“Good day James. You may call me Polly. I feel it prudent to let you know that this isn’t my face or body. For the same reason as yours, I felt it safer to use polyjuice for this meeting. If we reach an accord and agree to terms, I will of course be glad to show you my true self. I trust this will be agreeable.”

That surprised Harry, he hadn’t expected that anyone would be as paranoid about their privacy as he was. But as they were here…

“Thank you Polly, I understand the need for privacy. I have to be honest, I’m not entirely sure what possessed me to post the advert as I did. I actually didn’t prepare anything for this interview as I wasn’t even sure I was going to see this through until this morning. Is it ok if you just told me a bit about yourself, and we can take it from there?”

Harry didn’t miss the narrowing of Polly’s eyes at that, and gave a sigh of relief when she straightened herself up some more and didn’t immediately get up and leave.

“I can see why you said you needed someone to assist you. I would have been very disappointed if you had stood me up.” Her voice as quite but stern, reminiscent of a certain Professor McGonagall.  
“I graduated from Hogwarts with 5 OWLS. I was unable to complete my NEWTS due to the war and have no intention of doing that now. I was intended to be married, however my ‘betrothed’ fortunately did not survive the war. Due to the nature of my family and the ‘betrothal’ set up by my family against my wishes, I am finding it hard to find work. I am not a Dark witch and did not support the Dark Lord. However most employees can’t look past what they believe to be the truth.”

This didn’t surprise Harry as much as you’d expect. A lot of people from were facing the same problem nowadays. People still found it hard to trust easily.

“I understand Polly. So long as you are willing to take a vow that you did not support Voldemort, I will be happy with that. I’m not entirely sure what your duties would be. I would require that you stay in my house and assist me as needed. I do not currently work, and I’m not sure what I’d do if I did. Maybe you’d be able to assist me with some direction. I think for the most part I’d require some direction from you. That is something we’d have to discuss together if you still wish for the post. The salary would be suitably agreed between us. Food would be provided and a suitable stipend for any purchases required for your position. Do you have any questions?”

Polly seemed to stare off in space for a minute in thought before focusing back on Harry.  
“I have one question. How much control would I have? If I am to be the Mistress of the house I need to know how much power I would have.”

Harry’s eyes went wide at hearing her question put that way. Before he could respond she seemed to read something on his face, and stand. That seems to be in order then James. I shall accept the position. I will settle my affairs and owl your mail box for the address and start date. And with that, she turned on her heel and left the room.

Harry just sat with his mouth open. Shock permeated through him as he wondered what it was that he had let himself in for.

**********  
 **What am I in for?**

It was a week later that there was a sharp knock on Harry’s door. This was it. He was finally meeting the new assistant he had hired. He was finally going to find out who it was that he had hired.  
He had been nervous all week, considering all the possibilities. He had narrowed it down to only a few possibly Slytherins if he considered her comments on her family and her betrothed.

He walked through the entrance and opened the door.  
She was standing on the porch, in the shadows from the moonless night, and as he opened the door all the way her features came into view.

“Ch-o?” Harry stumbled over the words as the woman came into view completely. She didn’t seem shocked at all to see that it was Harry that opened the door.

“Harry. It’s been a while.” She didn’t bat an eye as she stepped inside, nudging past him into the house. “Take my trunk please. I hope my room has a bathroom.”

That seemed to snap Harry out of the surprise he was in.  
“Yes, of course Cho. It has a bed, wardrobe and ensuite. I left the decorating up to you.”  
Harry took her trunk from her hand as requested.  
Cho seemed to be studying the house around her, ignoring Harry as he took the trunk from her.  
“This is a nice house. Clean. It will do.”  
“Please direct me to my rooms so that I may clean up, and then we can discuss the details of my appointment.” And with that she started climbing the stairs which obviously led up to the rooms.

It took Harry a second to adjust to the abruptness, but gave a small start and rushed after her, meeting her halfway up the stairs and then leading her to her room, which was opposite his at the end of the hall.

*****

Harry wasn’t sure how things had evolved to this, but he wasn’t complaining just yet. So far he had gotten what he had asked for. He had a roommate. She was already giving him direction. Albeit not quite what he had been expecting, but direction nonetheless.

Cho found him seated in the small study down the hall from their rooms. She had changed out of her traveling clothes and Harry got his first real look at her.  
Her black hair was tied up in a tight bun that looked almost painful. Her dark eyes and high cheek bones were as beautiful as always with their oriental touch from her ancestry. Her body looked as toned as always, although from the quick glance, Harry noticed her breasts seemed larger than when they were in school. Which made sense. She was wearing a long ankle length dress that was narrow enough to show her curves but still kept her skin hidden.  
It was as Harry lifted his eyes back up to her face that he noticed her staring at him with sharp, stern eyes, with a hint of amusement.

“I trust that you have completed your study of my body.” She snarked  
Harry blushed deeply as he looked away.  
“Sorry, I didn’t mean to stare. I just haven’t seen you in a long time. You haven’t changed that much.” He stammered out avoiding making eye contact again.  
“You haven’t changed much yourself since 5th year. You are still small and thin, although h your eyes are still beautiful as always.”

Harry wasn’t sure if he should be blushing at the compliment or offended at the comments, however he was interrupted before he could decide.  
“So regarding my duties. We need to set some rules before we go any further.”  
Harry nodded in agreement which Cho took as her cue to continue as she sat down primly.

“You obviously need a lot of help. This house has obviously been renovated, however you yourself are in dire need of some grooming and clothes. We will sort that first. As to giving you direction, well that we can decide on later. But firstly, If I am to assist you, I require you to follow my every instruction without argument. Is that acceptable to you?”

Harry took a second to think about it, but ultimately, this is what he needed. He needed help, even if he wasn’t sure what help he required right now. So reluctantly he nodded his head. “I agree”.

And that was that. With a nod good night and a comment about meeting for breakfast, Cho stood up and left the room.

**********  
 **Caught out and the start**

The first month together had been uneventful. Cho had taken settled in easily and had spent the time getting to know Harry and trying to understand his needs and how she would be able to help him. She had nowhere else to go and this was as much for her as for him. She definitely got more of an answer for how to help after the incident….

**The incident**

Harry hadn’t any elves to help with the house.  
He had insisted on doing most of the housework himself. It was only the meals that were prepared by a private company and delivered right to the dining table as required and the cleaning company that swept through the house once a week cleaning, and dusting every room that assisted.  
It was whilst he was downstairs in the basement preparing to do the laundry that it happened.  
Harry was quietly humming as he sorting the clothes in the large washing basket that he came to a stuttering stop as he noticed what he was holding in his hands. The blood red piece of lace and silk could hardly be called a panty, but that is what it seemed to be. He snuck a quick look to the stairs before slowly opening the panties in his hand to get a proper look at it.  
He remembered doing laundry whilst on the run with Hermione and Ron, and never looked twice at her plain white full panty. These however were nothing like that. The panty seemed to be small enough that they would cover much of anything. It was quite startling to think that Cho had been wearing these in the few days since he’d last done laundry.  
It was as he slowly turned the small piece of fabric around, he noticed the small print on the inside claiming them to be Victoria secret. It was definitely a secret. He remembered the time Aunt Petunia made him wearing panties for a whole year, because that was the cheapest underwear she could find in the bargain bin at the time.

He could feel his dick start to stir as he kept examining the panties. He brought them closer and took a quick sniff, smelling the musty scent, there was a slight sour smell too, but wasn’t too off putting for some reason.  
He was quite startled to realize that he had dropped his own pants and boxers and had one leg already in the panty when he heard a gasp from the stairs.  
“What are you doing?” Cho stalked into the room, as Harry froze.  
As Cho stalked toward him, he managed to get his feet back under him and covered himself with his hands, which included the panty that was now half on him, up one leg.  
“Uh, Cho, nothing. Uhm-“Harry stuttered out.  
“It doesn’t look like nothing. It looks like you’re wearing my panties. Is that what you do every time you’re doing washing? Do you jerk off in them too? Do they turn you on?” She was now standing right in front of him, hands on her hips and looking down on him.  
This also happened to be the moment Harry noticed she was still taller than him.  
Harry had no idea how to explain the situation and just stood there, blood red panty around one leg, hands covering his crotch, as he stammered out nonsensical words.  
“You’re such a dirty little boy!” Cho said with a smirk as she examined Harry blushing.  
And for some reason that comment made Harry’s dick twitch, which made Harry’s eyes widen slightly and his blush to an even deeper red.  
“Well, there really isn’t much explanation needed I guess. If you prefer wearing panties, then who am I to deny you. You can keep those. We will go through your wardrobe and throw your other underwear away. Also a trip to the store is in order so we can get you all your own.”  
That declaration caused Harrys head to shoot up as he started at Cho in shock.  
“But, but, I don’t wear panties.” He managed to get out. Cho’s glance down to his crotch and the panties there seemed to cause him to stutter to a stop and blush once again.  
She seemed to take this as agreement, so gave a sharp nod, turned and left.  
“I will meet you in your room in 5 minutes. We need to take some measurements and prepare you for the shopping trip.” She called over her shoulder as she left.

*****

Harry returned to his room, hoping to avoid Cho until he could make sense of what was happening only to come to an abrupt stop as he saw her in his bathroom busy putting some bottles and creams down on the counter.  
He took a step inside the bathroom, a question on his lips as he was interrupted.  
“Right, come in here and take off your clothes.” Cho said as she continued going through the products she was laying out.  
She turned to him after a few seconds of not hearing him comply. He was just standing there with his mouth open. Too shocked at the command to move.  
She turned to him fully.  
“Harry. You told me when I started that you would do whatever I tell you. I am telling you now to remove your clothes. If you are going to ignore my ‘directions’ the very first time I give them to you, then I am done here.” She turned sharply and started out the door. “I will go pack my things” was said over her shoulder as she left the bathroom.

It didn’t take Harry long to think about that. He wasn’t sure he wanted to do this, but he definitely knew he didn’t want her to leave.  
“Wait. Please, don’t go. I.. I’ll do it.” And with that he slowly removed his shirt.  
It was as he got it over his head, he found her standing outside the bathroom door, watching him. Hand on hips. One eyebrow elegantly raised up.  
“I am only going to tell you once. You wanted a Mistress. Regardless of how you meant it at the time. I am now your Mistress. I will only tell you to do something once. The moment you question me. I’m gone. No second chances.”  
Harry was now standing in just his track pants, short on the floor, gaze down at the floor. He didn’t know what was happening, but she was right. He didn’t want to have to think all the time. He just wanted to do what he was told. It was at that moment that he realized that he wanted her to stay and if she wanted to give him orders he would do as she asked.  
“Do you agree, Harry?” Cho asked as she took a step into the door way looking down at Harry.  
“I agree.” Harry responded as he slowly lowered his track pants down with a dark blush, showing that he had indeed worn the Red panty as Cho had said he should.  
It was with surprise that Cho noticed and gave a soft chuckle as she examined his body. His hair was longer then in school, hanging over his ears and near his Jaw. He still wore his glasses, but they seemed to be the only masculine detail to his face. He looked extremely androgynous, which gave her all sorts of ideas. His body was thin and delicate looking. No real muscles to speak of.  
The panties seemed to be slightly big for him, which was surprising, his dick was obviously hard and tented with the head slightly peaking over the top of the panty.  
Cho took a slow walk around Harry as she continued to examine his body. He had a little hair sticking out around the top and legs of the panties to go with his slightly light colored, hairy legs. His bum was the only real curve he had, and seeing such a plump little bum seemed out of proportian. The panty was a Brazilian type, so went slightly between his arse cheeks.  
In all he looked like a teen girl slightly before puberty took hold properly.  
Her examination didn’t go unnoticed and the embarrassment caused by the inspection caused the blush to flow down Harry’s neck, and make his chest red too.  
“Very good. Now remove the panties too. I need to take measurements.

This panty doesn’t fit properly, and I need to remove your body hair. It looks quite off, to see hairy legs and pubes around a ‘sexy’ panty like that.”  
Harry only glanced briefly at Cho before he slowly slid the panty down his legs and stood up again, covering his dick and balls with his hands.  
Cho was ignoring this as she started looking through her tubes and bottles, and selecting one.  
She turned around to face him and noticed him looking at the floor as he covered himself.  
She gave a chuckle and pulled her wand out and touched it to the tube, “ _Calor_ ”.  
She then squirted a dollop of the now warm cream onto her hand, and started to rub in softly into the hair over Harry’s chest. She gave no notice of the flinch Harry gave as he opened his mouth to question her.  
“This is just some hair removal cream. It will be painless and will last a month. Don’t move” And with that the question died in Harrys throat. He didn’t dare move either. He didn’t want to do anything that might cause her to leave.  
She finished rubbing the cream over his chest and tummy, and under his arms and started on his legs. By the time she got to his hand covered crotch the cream she had already put on had started to tingle.  
She glanced up at him, and gestured to his hands, “You need to remove your hands. I promise, it’s not something I haven’t seen before. “  
With that being said, Harry slowly moved his hands away from his dick. Which was still hard and red and throbbing. He kept his eyes down on Cho’s face expecting a reaction. But other than a slight widening of her eyes, she didn’t react at all other than a slight lift at the corner of her lips, and then she started rubbing the cream over his balls and all around his dick. He didn’t dare ask what she thought, but was definitely curious.  
She finished up in front and then went to the back rubbing it in, all between his arse cheeks and against his hole. He gave a slight jump at the feeling of her fingers against his arsehole but otherwise didn’t move.  
Cho finished up with the cream, stood up and gave his body a once over to ensure she got everywhere.  
“You’re face looks very soft and smooth, do you even have to shave?” Cho asked as she took his chin in hand and tilted it slightly as she looked at the hairless skin there.  
“No, I haven’t needed to shave my face yet.” Harry murmured quietly. He was a little ashamed of that fact.  
“There, there. It’s not a bad thing at all Harry dear.” She gave him a pat on his cheek and turned back around to the counter.  
She took up her wand, turned to him and slowly started to murmur under her breath as she moved the wand up and down his body at all the places she had put cream. As the wand gliding just over the surface of the cream, it seemed to drop off his body like it was being sprayed off with water. The hair falling away along with it.  
It felt completely foreign to Harry as he was slowly de-haired. His skin felt like it was tingling at all the areas that he was slowly losing hair.  
“There we go. Isn’t that better. Now you just need to rub this cream on all over where you had hair every day after you shower to keep it soft and healthy. I will know if you don’t..”  
Harry didn’t like the ominous way that sounded and immediately took the cream with a promise to do as told.  
“Now, in order to get the correct size of underwear I will need to take some measurements. I will have to take all the intimate ones now to ensure you’ll fit into whatever style you prefer.” She gave a wry chuckle as Harry blushed again.  
She pulled out a measuring tape from behind some bottles and started measuring Harry from head to toe. She measured his chest, and his arms, his shoulders and wrists. She moved down and measured everything from his toes to his knees. It was as she got to his crotch that Harry was once again covering that she stopped and glanced up at him, a questioning eyebrow raised.  
Harry slowed moved his hands away again exposing his dick and balls to Cho who on her knees in front of him as he measured.  
She kept her eyes on his dick as she measure his hips. It was as she measured around his bum that her staring at his dick caused her to start frowning slightly. Which only made Harry more nervous.  
He cleared his throat slightly, wondering why it was so dry to begin with.  
“Is, *cough*, is there something wrong?” His voice was soft and worried as he kept an eye on her growing frown.  
“Wrong?” Her frowned deepened. “Well, not wrong really. I was just wondering if it was going to grow any bigger?”  
She promptly placed the measuring tape against his pubic bone where his dick started and pulled it to the tip.  
At reading the size she let out a large breath of air which subsequently caused his dick to twitch again.  
“4 and a half inches.” She fell back onto her bum as if she couldn’t quite comprehend that. “That’s fucking tiny. Are you fucking me!” She moved her eyes from his suddenly covered again dick and into his eyes.  
“There were all sorts of stories at Hogwarts about how you’re hung like a stallion. This is fucking ridiculous!! What happened to it? Did you get cursed?” She shot out as if in disbelief.  
Harry’s embarrassment seemed to grow along with her ire as he stammered out a reply.  
“This is how big I’ve been since 4th year.” He flinched at her gaze. “I don’t know who said I was hung like a stallion. No one has ever seen me naked.”.  
That definitely got a response from Cho. She stumbled to her feet and moved so closed to him that if his dick twitched again she’d feel it.  
“Are you telling me? That you’re a fucking virgin? Seriously?” And then she started laughing, she started laughing so hard she had to lean down on the counter to keep her feet.  
Harry didn’t feel like he could be any more embarrassed then he was right now. Until her next comment.  
“I’m going to break the fucking boy who lived.” She turned to him with mirth in her eyes. “I’m going to do things to you that you wouldn’t believe.” And at that she left the room while chuckling all the while.


	2. Shopping

**Summary for the Chapter:**

> Cho takes Harry shopping. They both get more then they expected

**Shopping**

Harry was quite surprised at the size of the store that Cho took him to. Harrods. He had of course heard of it, but had never seen it himself. He hadn't realize that Cho had anything to do with muggle London in general as he believed her to have come from a pure-blood family line. The store was incredibly large, there were numerous levels going up, all with a number of escalators in the center of the atrium going up to each level. There was bright lights of the various sections and various perfume smells in the air predominantly coming from the little kiosk counters spread out through the various open spaces with sales people standing around with little sticks of paper. 

Truth be told, as much as Harry thought Cho might be new to the muggle world, this was the first time that Harry himself had been to a mall of any kind. His only experience with stores of any kind had been going to the grocer with his aunt, where he stayed in the car and only got out to pack and unpack the groceries as required.

He was feeling quite overwhelmed by all the smells, sights and sounds around him, but gamely walking along behind Cho looking all around him. He came to an abrupt stop though as Cho started walking into a huge area labeled "Luxury".

The entire section as far as he could see was all underwear of various kinds and styles. There were all the colors he could imagine, red, blue, green, neon colors. Panties that looked plain like Hermione wore, and small panties that looked like they wouldn't cover anything at all. There were section labeled with signs like, Agent Provocateur, Victoria Secret, Calvin Klein, and many more.

Harry just stood frozen to the spot as his eyes took in the sight before him. He knew of course he was being forced to be here. He had chosen to put on Cho's panties. He had made that choice and that had led to this. He wasn't sure if he was being punished or rewarded. His brain was all muddled and wouldn't even have been able to come to the mall itself if Cho hadn't expressly told him to.

"Are you going to stand there and stare or are we going to actually enter the store and browse?" Cho seemed quite amused as she came to a stop in front of the frozen Harry.

Harry gave a little start at her question as he pulled his eyes to her, "I didn't even know that you went shopping muggle London. Most pure-bloods don't."

"Hah, you'd be very surprised how many pure-bloods come shopping in Harrods. They do make superior underwear. Most magical tailors still make underwear at all anymore due to lack of interest these days. If you're lucky we may even bump into one or two woman you may know in here." She said, and gave a laugh at Harry's startled look as his eyes darted around suddenly trying to see if there was anyone he recognized or that might recognize him.

Fortunately he couldn't see anyone at all.

He was surprised as Cho took hold of his hand and started to pull him into the store proper though.

"Come on then. We have a lot of work to do. We need to decide what your favorite style will be and then select a number of panties for you, so you don't keep wearing mine. Naughty boy."

Harry started blushing at that comment that he was sure was said much too loud, judging by the smirking woman they just walked past. 

"Cho, shhh, please don’t talk so loud." Harry hissed out quietly as he was dragged along, his head down, to avoid noticing if anyone else had heard her. 

Cho came to a stop suddenly causing Harry to glance up quickly to avoid walking right into her. His eyes widened as he saw why they stopped.

"Sophia, it’s so good to see you again." Cho said as she dropped Harry's hand and grabbed the tall, beautiful woman in front of her. "You are just the person I was looking for."

"Cho, always nice to see you. You can't possibly need new undies already. I just outfitted you a month ago. What have you been up to darling...? Nothing too naughty I hope." This was said by the tall, blonde haired woman as she hugged Cho back and kissed her on both cheeks. A naughty grin on her face as her eyes sparkled. 

"Not at all. I'm not actually here for me, you see. This is my new employer, Harry." Cho gave a glance to Harry as she introduced him to Sophia.

"I caught him in my favorite pair of Victoria secrets, so I decided we'd get him his own pair. Maybe you could help him choose a style. He's new to all this."

Cho still hadn't lowered her voice and Harry was sure that half the store had probably heard her comments. He felt like he wanted to just sink into a hole as Sophia turned her eyes to him. She seemed first startled at Cho's comments, and then suddenly her smile turned predatory as she eyed him up and down.

"I see. Yes, I see. He definitely has potential. Maybe a little work." She started to take a slow walk around the blushing Harry as she examined him from top to bottom.

"Right, let’s get him in a booth and we can have a look at the styles and see what we have to work with," Sophia gave Harry’s arse a little slap and grinned at Cho as they each then grabbed a hand each and started pulling Harry to a cubicle.

It was just like an open little office, there was a computer on a small table with a large screen, and there were three walls with no door, so anyone could look into the little booth.

"Right stand over here darling." Sophia said as she directed Harry to a spot on the floor.

There seemed to be a little camera on both the front and back of the spot he was standing in currently.

“Don’t move darling Harry, or I might have to punish you.” Sophia gave a laugh at Harrys wide eyed expression

"We never used this with you Cho, but this is some new technology we have recently gotten. We will take a scan of our dear doll,*ahem* I mean Harry's body," She gave Harry a sly grin and a wink. "And then this screen will show a 3D representation. We can then add and remove various styles and colors to our hearts content and determine what fits him best."

This was all said as the little camera started whirring and scanning up and down Harry's body. He stood stock still, too worried to move.

Sophia seemed to be as formidable as Cho was when she was acting stern. He didn't feel like upsetting either one would bode well for him.

He glanced up as the screen lit up with a completely hairless body on it. It looked almost like a mannequin with no dick or shape to the chest, no ears and no actual fingers.

He was actually a bit surprised at the image. So that was his body shape. That was interesting looking at it from this perspective. The little image rotated slowly, and Harry could see the plump bum he had and flat chest that seemed a little weird on the same body.

“So let’s see what we like, shall we?” Sophia asked Cho, as she started tapping on some keys.

“So according to the software, our dear Harry has a rectangle body shape, however those hips and arse are borderline hourglass.” She said with a giggle at Harry. “Right let’s see…”

There appeared to be a catalogue popped up on the screen of various types of plain white underwear that seemed to cover and expose a whole variety of different parts.

“Mmm, that arse and hips, definitely thong style, I think.” Sophia asked and glanced at Cho as she giggled.

“I agree, that bum needs to be showed off. It’s the best part of him.” She giggled again as she noticed Harry’s blush as he still stood frozen to the spot staring at the screen.

“Maybe a tanga, specifically.” Sophia muttered quietly as she started flipping through the various underwear and after a click a plain white tanga appeared on the 3D model.

Harry’s mouth dropped open slightly as he took in the sight of the plain mannequin, with what seemed to be a very sexy arse in an equally sexy pair of panties. He was quite surprised by how good it looked on the image and he had to admit to a little thrill that shivered through his body when he realized that’s what his bum would look like.

He was oblivious to the two woman who were whispering excitedly and giggling as they kept switching glances between Harry and the image.

Harry’s attention was drawn back to the two woman as he heard Sophia’s next comment. It was loud enough he was sure others in the store also heard it.

“Actually, it looks a little odd don’t you think Cho. Let me try something.” Sophia gave Cho a sly glance with her mischievous smile back in place as she pressed a few more keys.

Harry glanced quickly back to the screen that Cho was watching intently when he noticed her eyes widen and her mouth open and she licked her dry lips.

He didn’t noticed immediately what she was staring at until he glanced up and as the model completed its rotation he noticed the matching bra on the body. It wasn’t the bra that seemed to have caught Cho’s interest though.

It was the slightly large breasts that were filling the bra that seemed to have surprised her.

Harry’s first thought was that it actually seemed to suit the model perfectly now. Almost like it was something that was obviously missing. His second thought was one of shock as he realized that he was having these thoughts about a model of him. He realized that he thought he was missing breasts, and that caused him to stumble back a step in surprise and a little fear,

What the hell was happening to him?

After clearing her throat gently and glancing at the grinning Sophia, Cho managed a response.

“That actually seemed weirdly appropriate.” Sophia grinned even wider at that.

“We will definitely need to get some bra’s to match. It would be a crime not to.” Cho seemed to get a sparkle in her eyes as she made that declaration.

“I just happen to have some new silicon cups lying around that would be perfect.” Sophia got up and left abruptly as Cho turned to Harry.

“Are we going to have a problem with this Harry? Are you going to follow my directions as you agreed?”

Harry tore his gaze from the screen to look at Cho. He noticed her stern face and tried to shake off the nervousness he was suddenly feeling. He wasn’t sure if he wanted to go this far. He was firstly terrified of being caught by someone he knew, but also in the back of his mind, he was extremely turned on by the idea. He suddenly realized his dick was straining in his panties Cho had given him. He could feel the way it was rubbing against the lace and the slick of the leaking precum.

“No Cho. I will follow your directions.” Harry admitted quietly as he looked back down to the floor, half to hide his shame in his eyes, half to hide the blush creeping into his face.

Cho gave him a grin as she stood up and started to pull Harry along with her to the changing rooms. On the way they met the ever grinning Sophia.

“Here we go Cho, I’ve included the molding glue. Once it’s been placed, Harry dear, will need to wear a bra to keep them in place. They should set properly within an hour.” She gave Cho a small white cardboard box with a fancy label and design on it.

“If he looks as good as we both think he will, you should consider a more, permanent option.” Sophia said with sparkly eyes and a large grin as they walked past her. She gave harry another swat to his arse which caused him to give a little squeak and jump, causing both woman to burst out laughing and his blush to intensify even more.

It took Cho only a few minutes of work to stick the silicon breast molds into place on Harry’s chest in the changing room. She then used the disposable bra included to keep the mold in place. It didn’t look like much until Harry put his shirt back on over the top and Cho noticed the distinct C- cup breast that tented his shirt and left the front of it, hanging baggy like over the breasts.

It wasn’t her original plan, but she couldn’t help but admire his body more now with his perfectly shaped “breasts” and juicy arse. She definitely liked him more like this then she’d imagined she would.

Harry himself seemed to be in quite a bit of shock himself as he stared at himself in the mirror.

**********************

What followed next was both exciting and humiliating.

Cho dragged Harry around the store, showing harry a variety of different styles and colors of underwear. She did stick mostly to the Tangas and Thong styles, but browsed throughout, commenting loudly to his eternal embarrassment for all to hear.

“Look Harry, this color is perfect for you, don’t you think?” Cho asked as she held up a baby blue lacy tang against his body.

“Oh wow, this would be perfect Harry dear, you’ll love the feel of this silk on your bum.”

“These beads on this thong will feel like heaven against your hole, Harry”

“This thong seems like it will hold your little dick perfectly, don’t you think Harry?”

“Do you think you’ll need a crotch-less panty like this Harry?” She asked holding it up at eye level for all to see.

These comments were made frequently as the stormed around the store as Cho piled Harry’s arms high with all sorts of panties and bras of various shapes and colors.

His face was blood red and his eyes were permanently on the ground as he followed Cho. He heard the woman all around the store giggling at him as they passed and outright laughing at some of the comments Cho was making as they went.

The worst part was that with every humiliating question, she didn’t stop until he gave her an appropriate answer. So having to agree to her various comments made him feel both extremely embarrassed and turned on which was frankly, confusing as hell.

He didn’t even notice when they’d made their way through the clothing section and was surprised when they got to the changing room with an armful of both underwear and some skirts, tops and dresses.

He woke from his self-induced zoning out at Cho talking to him as they entered the change room.

“Harry, take off your clothes and put these on. I want to see how they fit you’re ‘new’ body.”

Harry glanced at the undies in her hands and opened his mouth to respond, but was beaten to it.

“If you are about to say anything except, ‘yes Cho’, then we are done. I have been very patient with you Harry, but I’m getting tired of your hesitance. If you are going to continue questioning my every direction, then I am going to require an oath from you.”

Harry glanced up in surprise. He knew he didn’t want her to leave, but he also didn’t want to have to make some sort of oath. So far he had strangely enjoyed their time together, and something in the back of his mind was extremely excited by this turn of events.

He glanced at her serious expression briefly.

“Yes Cho.” Was all he said, as his shaky hand reached out and took the bright blue panty and bra from her.

He slowly stripped off his clothes, and started to pull the panty up his legs. He couldn’t help but breathe out slowly at the strange feeling as the soft material slid up his smooth and hairless legs. The measurements Cho took were obviously perfect as the panty settled around his hips and around his bum perfectly. He glanced at the mirror for a quick look at himself and dropped the bra in surprise.

He was shocked. The panty was a bright blue lace Tanga. The front pocket covered his whole dick completely even though he was rock hard. There was lace across the whole front and it was seamless. The silk started at around his balls and stretched slowly up the back between his arse cheeks. He turned slightly and saw the way the silk cupped the small inner section of his arse. It looked perfectly.

He couldn’t believe this was him.

He bent down to pick up the bra, never taking his eyes off himself, and suddenly gave a slight wince as the material between his arse slid in deeper and rubbed against his hole. It felt slightly uncomfortable as he stood up again.

“I know it might feel a little uncomfortable now, but these high quality panties are much better then cotton ones rubbing against your arsehole. Believe me. You’ll get used to it quickly. Promise” Cho said as she examined him and noticed his wince.

Harry slowly lifted the bra up and looked at in in confusion before turning his confused face to Cho.

She noticed his face and smiled briefly. Here, let me help you with that. We’ll teach you to put on a bra properly at home.

She quickly removed the disposable and put his arms quickly into the holes and before he could blink it was in place and hooked up. He immediately felt a little itch at his back where it latched but refrained from shifting too much as he took in his appearance.

The bra matched the color of the panties and pushed his silicon boobs together creating a slight bit of cleavage.

If he didn’t know he was looking at himself he would have thought that everything from the neck down were a perfectly sexy woman. That thought definitely caught him by surprise.

It didn’t take much after that to get him into a long pencil skirt and a plain white blouse that felt a little tighter then he’d ever worn before. The surprising thing was that he didn’t feel any different in the woman’s clothes then he would have in normal men’s clothes. He definitely looked feminine from the neck down though. Lastly Cho placed a pair of black pumps down for him.

After looking him up and down and licking her suddenly dry lips again, Cho pulled the tags off his clothes so she could pay, grabbed up the rest they wanted to buy and walked out leaving Harry spluttering.

“Come on Harry, let’s go pay. We have another stop or two to make before we head home.” And off she went.

Harry had no choice but to follow along behind her, dressed as he was. He caught up to her just in time to hand over his expense card to the teller so they could charge it to his new Barclays account. 

Harry then, carrying all the bags of clothes followed along behind Cho as she swiftly walked from the store and entered another one across the hall.

Harry abruptly realized that it was a makeup section and believed Cho wanted to pick up a few things for herself.

He was wrong.

He stopped next to Cho in time to hear her finished her request to the woman standing next to a makeup vanity.

“… So you see Bev, I would very much appreciate assistance with his makeup, it’s his first time after all and I want him to see what’s possible.”

Harry gaped at Cho and then then turned to the woman. Bev.

She seemed to be quite amused by his expression before seemingly making a decision.

“He looks perfect, Cho. Let’s get him in the chair and see what magic we can do.”

Harry realized exactly what was going to happen. Female undies were one thing, woman’s clothes were another. But makeup was the line. He turned to Cho, prepared to voice his denial of this step, but one look at her raised eyebrow and thin lips had his shoulders slumping. He placed the parcels down and slowly reluctantly climbing onto the seat in front of the vanity.

“Right, let’s get started.” Bev said as she removed his glasses. What prescription are these monstrosities she started to ask, then changed her mind.

“Clarke, take these to Sue at the Optometrists. Tell her we need suitable contact lenses.” The man who seemed to be Clarke appeared as if out of nowhere and disappeared with the glasses, holding them away from himself as if they were offensive.

Bev immediately called over someone else and whispered to her as they kept shooting him glances. After a minute of this, Bev started to pull all sorts of tubes, blushes, brushes and creams out as the other woman set upon his hair. Harry had to quickly close his eyes as Bev started rubbing something into his face and he decided to stay that way until they were done.

He didn’t know if it was to try keep himself calm during the process or to maintain the surprise until they were done.

It was about 30 minutes later when the woman finished and Bev had him open his eyes so she could help him place the new contact lenses.

He blinked a few times and opened his eyes slowly adjusting to being to see clearly again, and the first thing he saw was Cho’s face.

She was sitting opposite him with a cup of tea, the cup tilted sideways almost spilling the left over contents as she stared at Harry open mouthed. Her eyes wide and supirsed.

She exhaled slowly and gulped.

Harry quite enjoyed seeing her openmouthed expression for a change as he knew that was his face for most of the day.

“Harry, you look gorgeous. Truly.”

And at that Harry was swung around and took his dfirst look at himself.

At first he just stared, his brain not quite connecting the face he was looking at as his, but then it clicked.

That was him.

That dark haired, green eyed beauty was really him.

She had jaw length dead straight, shiny hair. One part was pinned up over behind her ear. Her eyes had subtle makeup making her eyes look bigger and almost innocent.

Her cheekbones were shaded to show them off perfectly.

Her lips, were shiny and a light red color. They looked soft and plump.

He was in awe at the way he looked.

It seemed Cho was too.

What would this mean for himself though? He was a man. He had a dick. But he looked exactly like a woman. No one would believe what he was hiding in his panties if he went out like this.

He was worried about the fact that he really like the way he looked.


	3. Start of training

They had returned home from the Mall while Harry was made up to look like a woman.

His hair was straight and soft, one parting neatly combed behind his ear. His eyes were unencumbered by glasses, the bright green eyes shining out at the world, wide and innocent. His face soft and smooth, plump lips shining with the light gloss on them.

The Pencil skirt was tight enough to show the slightly round hips and the rather nicely displayed bum. White blouse showing a hint of cleavage and just the tops of the bright blue bra sticking out.

Harry was extremely surprised by the looks he was getting, from both men and woman as they walked through the mall towards the exit.

The looks of lust and desire and envy sent his emotions and thoughts out of control.

He couldn’t remember the last time he had walked out in public and not looked on with admiration or fear from being known as the boy-who-lived or later the-man-who-conquered.

At this moment, in this time, he was anonymous to the people around him, and the looks they were giving him were based on what they could see at this point in time.

They knew nothing about him or his past.

It was terrifying and thrilling and it was something he never expected.

It was this moment his life had changed forever.

It had been 3 months since the shopping trip that had both confused and changed Harry’s life forever.

After getting home and receiving an overwhelming number of compliments from Cho, and even a slightly soft kiss on his lips as she went to bed, he had decided that when he was home he might try dressing a bit more like he was.

Cho had loved his decision and had gave him numerous lessons on doing his makeup and developing a proper bath time routine involving the hair removal lotions and makeup removing spells.

In the 3 months since that day he had turned into a part time woman with Cho’s wholehearted encouragement. The encouragement and pure joy she had showered him with whenever he came down for breakfast dressed as feminine as possible had definitely driven him in this as well as the thrill he got.

He still wasn’t comfortable going out in public as he was, but he did give into Cho’s demands and puppy eyes on occasion, where they went to do more shopping or visit a coffee shop. There was also the one time he had been dragged along to a spa for some “female” bonding.

Let’s just say the masseuse was probably about as surprised as Harry was when she discovered he was in fact not entirely female.

All in all it was an interesting time for them both.

Cho had started enjoying the power she could exhibit over Harry and he had started to enjoy giving in to her demands.

The light kiss she gave him all that time ago hadn’t been the only such Harry had received.

It did open the door for more…

*****

“Harry, we need to talk about the kiss… I don’t want you getting the wrong idea.”

Harry had just entered the dining room for dinner when he heard those words. It was only a week ago that Cho had kissed him after their shopping trip. He couldn’t help that he had spent a lot of time wondering about it and what it meant. So this conversation was long due.

Cho stood up after delivering her opening comment and led Harry into the sitting room, where she sank into the wide arm chair as Harry took a seat on the sofa, sitting near the edge as he gave Cho all his attention.

“I can’t lie and say I haven’t wondered about it, Cho, but I figured if it meant anything, you’d let me know.” Harry couldn’t help looking down as he said that.

“The kiss was a bit of a surprise for me. I didn’t plan it, but I was so proud of you, and happy at what you accomplished, and of course you looked sooo sexy, I just couldn’t help myself.”

Harry naturally blushed bright red at that, but also felt a burst in his chest. She was proud of him..

“I have to be honest Harry, I don’t think there can be a normal relationship between us.” Cho said seriously as she kept her gaze firmly on Harry

“I prefer, a more… dominant man… as a boyfriend.”

Harry felt a stab of hurt at that. He didn’t think he was dominant, but that didn’t mean he was submissive did it.

“But in saying that, Harry, I am you’re ‘mistress’ as you put it in your advert,” She smirked at Harry as he flinched at that. “But that doesn’t mean we can’t be girlfriends and even mess around occasionally if you are ok with that.”

Harry glanced up at Cho at that, in a bit of shock. He completely ignored the ‘girlfriend” comment, and focused on the important part. She wanted to mess around? That sounded good to him. He couldn’t deny that he had wanked off to thoughts of Cho a lot since she moved in.

“That sounds fine Cho. It’s just, you’ll have to help me, if that’s ok.” Harry said quietly, looking everywhere but at Cho.

Cho liked that answer, but his shiftiness had her a bit confused.

“Harry,” She waited till he met her eyes. ”You have had sex right?” Her eyes widened as he immediately flinched again and looked away.

“Oh fuck me,’ she whispered quietly as she noticed his flinch to that. “Harry Potter. The-boy-who-lived is a fucking virgin.” She got up and started pacing as she swore under her breath.

“I would have thought that you were having sex left and right… I know you said no one had seen you naked, but I have to admit I didn’t completely believe you.”

Cho continued to pace up and down, “Breathe Cho, breathe….”

And she slowly came to a stop as her face brightened. Her eyes widened as she suddenly came to a conclusion.

Harry saw the grin slowly spreading on her face and to be honest he was a little un-nerved by it.

“Cho, are you ok?” Harry asked quietly as he slowly stood. He wasn’t sure if he want to step closer to her or take a step back.

“Harry,” she said as she turned to face him. “You promised you’d follow my every direction. And I’ve very impressed at how well you’ve done. I’m very proud of you…” She said as she observed his reaction. And her grin got bigger at his noticeable shiver at her words.

“We’ve agreed to be girlfriends, and as your girlfriend I believe it’s my job to teach you. You’re a virgin, and to be honest, I have a lot of experience. So we’ll be taking things to a new level.

She kept her gaze on Harry, he gave it a bit of thought, but of course if she was talking about what he believed she was talking about, he wasn’t going to deny this opportunity to pass.

He gave her a slight nod of agreement.

That was the sign Cho was waiting for as she immediately moved closed and gave him a deep kiss.

She moved away and started to pull her top slowly up her body. Harry couldn’t take his eyes off her as she exposed more of her tight tummy, she had definite abs, and a sparkly pink little heart hanging in her belly ring became visible as the shirt passed her belly button. Her large D cup boobs stretched up as her shirt continued rolling up, and then bounced down, almost violently as they pulled free. The shirt landed somewhere on the floor.

Harry didn’t notice, as his gaze was fixed on the first real pair of boobs he’d ever seen. Her nipples were large, much larger than he expected, and they were hard, and pointed and he licked his lips at the thought of biting on them. He didn’t even notice his dick immediately getting hard in his panty and started to leak.

Cho appreciated the reaction in Harry, and honestly had never had a bad reaction, or negative comment from her breasts before. The girls in her dorm at Hogwarts had loved sucking on them, and she had to admit it had become a source of pride for her.

She slipped the pumps off her feet and slowly lowered the pajama pants she was wearing down her thighs.

Harry immediately pulled his eyes away from her thick nipples, and perfect boobs, as he noticed her starting to lower her pants. As they cleared her hip bones, he gave a shiver. The slightly plump mons become visible when he noticed something dark and moving slightly to the left of center.

He gave a little start as he realized that he was looking at a small moving tattoo of a snitch. It was perfectly drawn, with little fluttering wings, and it seemed to move around in little circles slowly as if waiting to be caught.

His admiration of that surprising development was brought to a halt as Cho kicked her Pants to the side.

She loved seeing the look of awe on her face. If nothing else, he definitely made her feel superior when he looked at her like that. It almost looked like he’d start drooling soon.

“Come closer Harry, I’m about to give you your first lesson.” Cho said as she lowered herself back down onto the armchair behind her. As she sat down, she spread her legs slowly and lifted one leg onto the arm rest, exposing herself completely to Harry’s gaze.

Her pussy was completely hairless, and the slit seemed almost too tight to his eyes, until she sat down and opened her legs. Then he couldn’t help the shiver he got as the slit started to open up before his gaze. Her clit become visible and looked quite prominent and hard to miss as it peaked out between the top of her folds. As she settled down comfortably, you could see the slightly circular hole in the center of her pussy, as she gaped ever so slightly.

“Get your clothes off, and get down on your knees so you can take closer look.” Cho said softly as she beckoned him closer with a finger.

It didn’t take Harry much time at all to get undressed and on his knees in front of her. He was wearing a light pink thong with little white peals between his arse cheeks, and a matching bra holding up his silicon assets.

He was on his knees, moving closer when the smell hit him first. It was a slight musk, and had a slightly sour tang, but wasn’t off putting in the least.

“You’re going to eat my pussy Harry, and you’re going to keep going until I cum. If you stop for any reason, we will have to think of a suitable punishment. Do you understand Harry?”

Harry just glanced up once to Cho’s face before looking back down to the gorgeous sight before him.

“I understand, Cho.”

“Right, so then let’s see what you have Harry. It’s your first time, so I will be giving you instructions as you go.”

Harry gave a slight nod as he moved closer, hesitantly. He gave a soft sniff as his nose moved to within inches of her open and glistening pussy, and shivered at the smile again. His eyes caught the little snitch moving around above her clit for a second, then he poked his tongue out. He just poked his tongue straight into the hole for a second, tentively almost to taste it. He pulled his tongue back into his mouth, ignoring the slight string of glistening wetness that was hanging from his tongue to her opening.

The taste wasn’t bad. He could try more, and with that he slowly gave her a lick from the bottom of her pussy, sliding his tongue gently between her slightly open lips, and up, right over her clit, just like licking an ice cream.

Cho gave a jump at that, “That’s good Harry. Keep doing that for a bit.”

Harry didn’t need any more encouragement then that and kept going up like that, he was getting more enthusiastic at his efforts. It was this enthusiasm that caused him to get a bit out of control, and he suddenly had a different taste as he licked. He tried again as he went from bottom to top, and realized that he was starting from a bit lower then he started and was starting to lick up all the way from Cho’s anal. She didn’t seem to mind it judging by her moans and words of encouragement, so he just ignored it and kept going. At one point he slowed down and wanted to get a bit more of the juice leaking from her pussy, so stuck his tongue into her slight hole, which gave way easily and he curled his tongue as much as he could and scooped the juice out. He kept doing this, and started to get a more accurate taste. It was definitely a bit tangy on his tongue, but he couldn’t help tasting more and more.

His efforts were eventually stopped by Cho, as she gave his hair a slight tug, trying to get him to move his mouth up.

“Jus-just suck on my clit. There, Right THERE!!!” she moaned even louder and started bucking a bit as Harry covered her clit with his mouth and gave a suck. He kept sucking and darting his tongue out every now and then as he gathered a breath, until with a shout and an even larger buck, he felt his mouth and face getting flooded with cum, as Cho gave into the orgasm that she was riding through. He immediately stopped and started to pull away before Cho grabbed his head and shoved him back.

“DON’T YOU FUCKING STOP SUCKING!!!! She gritted out as she kept riding through another orgasm.

Harry was a bit startled but kept sucking, and swallowing as much of the sticky juice as he could. He could almost feel his throat coated with the sticky slimy juice.

But kept going. He had sucked for another 5 minutes before Cho eventually pushed him away from her pussy and gave a deep sigh of satisfaction.

“That, Harry dear… Was very good. You are a natural little pussy sucker. I think we’re going to have a lot of fun together.”

And that was the start of the training.

**Notes for the Chapter:**

> I appreciate every one who reads this. If you are enjoying this, please let me know. If not I'd appreciate knowing that too. I am in no way a professional. I am purely writing this because it's something I would have loved to read myself.


	4. Chapter 4

**Summary for the Chapter:**

> This is just a short filler to set the scene for the next few chapters

It had been an incredible three months for Harry.

He spent alot of that time between Cho's legs. But that just made it all better.

He even learned a bit of a trick to it.

Anytime that he happened to spent extra thought on his clothes, or just got "caught" in especially sexy panties, then he was forced to make Cho orgasm. 

She had yet to get him off, but at this point he wasn't complaining. He enjoyed eating her out as much as she did. Things had even developed to the point where she let him more purposefully lick her tight anus for a while. He had taken a strange liking to it since the first time he made her cum and had accidentally tasted it.

Truth be told, that's what probably led him to his current situation.

*******

He was lying in his large bath just relaxing. This was the last day his silicon breasts would last since they were place on him. Cho had told him the glue would be wearing off any day now, so he was enjoying his last time with them. He loved the way they would hang down slightly to the sides of his chest. They weren't that big, and if he ended up replacing them, he might even go bigger, but for now he quite liked them. 

He was just relaxing with his eyes closed, thinking deep and naughty thoughts when he heard Cho come in to his bathroom.

"Hi Cho. Did you have a good time shopping?" He asked as he opened his eyes and sat up so he could face her.

She came in and took a seat on the closed toilet lid.

"Hey Harry. I always have a good time shopping. Especially when spending some one elses money..." She chuckled softly. 

"I actually have a surprise for you because you've been so good the last few months. There are two suprises actually, one good and one bad. Come get it when you're ready."

With that, she stood up and left, leaving Harry both nervous and excited. 

Anytime Cho went shopping she'd usually buy him a few panties or skirts too, but it was never a surprise really. He wondered what she'd gotten now.

He rushed through his cleaning routine, gave his hair a quick wash and jumped out of the bath.

He was in such a hurry, he just ended up using his wand to dry himself, and slipped into a pair of white silk cheeky panties and a bra, and throwing a slip over the top.(The slip was another gift he'd previously gotten from Cho, to sleep in"

He rushed through out to her room, and slowed to a walk just before her door.

He gave a knock and quietly entered to see her sitting on the small sofa in one corner with a few packages lying on the low coffee table.

"Come in Harry. Have a seat, and let me see where I put your gifts..." She said as she stood and started rummaging through the parcels.

"Aha! Here they are." She said as she pulled out two wrapped, plain white boxes with a black symbol of a cat on them. 

"Here, open this one first." She handed him the longer package. 

Harry took it gently. This was different to the other times when she'd buy him gifts. Usually he'd just walk in and see the clothes she bought him neatly laying on his bed. 

As he started to open the box, Cho seemed to get a little excited and moved on her seat, until she was sitting right on the edge watching Harry intently. 

"W-wh- what is this?" he asked in surprise once the box was open and he removed the little device. It was glossy black and made of a sturdy wire. there seemed to be some sort of hinge and a latch.

"This my dear, little Harry, is your the bad surprise." Cho moved onto her knees so she could scoot closer to Harry. "This is a chastity cage. Its part of your training of course."

Harry gave a start at that. He had of course seen some porn magazines under Seamus' bed at school so he had seen something like this before. But locking up him dick, he wasn't sure about that.

"Let me explain Harry, We will be moving onto a new part of our training, where we can start teaching you how to receive pleasure. But to do that, you will need to wear this for me." She gently took the cock prison from him and opened it. "This isn't a punishment Harry, its a reward. Just try it for me. You want to make me proud of you don't you?" She asked as she gave him a wide eyed look.

He knew she was playing dirty, but he did want to make her proud, so saying that he slowly lifted his bum off the sofa, and slid his panties down exposing his hairless dick. 

It was soft at the moment, but was already leaking a little pre-cum, as it always did when he was wearing panties. 

"That's a good boy. It took me a long time to find the magical sex shop, so I hope you'll enjoy this as much as I do." She said as she gently took a hold of his dick.

It shouldn't have been a surprise to anyone that it immediately started getting hard. The pre-cum was pouring out the tip now.

"Oh dear, that wont do at all. You need to be soft to get the cage on. Would you like me to take care of that for you Harry?" Cho asked sweetly as she kept a firm grip on his dick. 

She did well to keep the grimace out of her voice at the size. Holding it in her fist as she was, the tip didn't even stick out of her hand. He was fucking small.

Harry was quiet taken aback at the offer. "That would be great Cho. Thank you"

Whatever he expected, it wasn't for Cho to let go of his dick, grab hold of his balls and pull them down with a hard yank

"Yooowch, FUCK Cho, what are you doing." Harry cried out as he tried to move out of her grasp. 

She wasn't having any of it. She kept a hold of his balls, turning them this way and that as she kept an eye on his dick as it suddenly starting going limp. As it got back toits small limp state she released his balls and quickly slipped his dick into the metal cage. As soon as he was in, she slipped the metal ring around his shaft, and around the back of his balls and touched the two rings with her wand and muttered under her breath. 

There was a slight flash of light as the ring and cage welded together, and become one solid cage. no hinges or opening visable.

"Mmm, this was the standard size model, but we'll have to make it smaller. It still seems to big." Andwith that she gave it another tap of her wand and muttered quietly. 

Harry could only watch in shock as the cage shrunk down until it framed his limp dick perfectly in a downward curve.

"There we go my little boy. A perfectly imprisoned boy clit"

That startled Harry. "A boy what now. Come on Cho -"

"Here's your other gift Harry. this is the good one that will help you have the most amazing pleasure." Cho cut him off before he could finish his complaint. 

She handed him the second box which he took nervously. 

He opened the box slowly, but had an idea what was inside already, so want surprised to find a small gloss black butt plug. The widest part was probably only just less then two fingers wide and it had a clear jewel on the end. 

"See, isn't it amazing. It's matching. And the jewel will of course change to match the color of whatever underwear you are wearing." Cho spouted enthusiastically as she seated herself back on the armchair. 

Harry just examined the plug slowly as he turned it around in his hand. Cho wanted him to insert this in his arse? He wasn't so sure about that.

"So Harry, let me explain the situation. That cage over your small little dick, cannot be removed by anyone but me. As you can see, you cannot even touch your dick, so that means you'll have to sit down to pee too. Isnt that just perfect." Cho grinned happily, as if it was the best thing ever.

"Now that you can't wank so much. And I know you've been wanking that little toy of yours alot, you will have to find other ways of getting off. That's what the butt plug is for. We will eventually be exploring the fine arts of anal orgasms. But your virgin arse is too tight, so I'm going to give you a week to prepare using the plug I've given you. You will have to insert it yourself, and wear it as much as possible. I will be doing random inspections, and for every time I find you wearing it, you will receive a reward. Also as you are preparing, every two days I will be making it slightly larger. So that when we have our first anal experience together, you will be ready for me."

Harry sat dead still getting more and more horrified at the idea. He was still holding the plug, but it seemed to get bigger in his hands the longer he stared. 

"Don't worry so much Harry. Have I done anything so far that you havent ended up enjoying. Just give it a try. Trust me."

And with that, Harry gave up the fight before it even began. He knew he would try it, just to make her happy.


	5. Chapter 5

**Summary for the Chapter:**

> Harry gets to experimenting

**Notes for the Chapter:**

> I apologize in advance that the writing isn't great, but hopefully you can overlook that for the content instead.
> 
> I'm not sure if anyone out there is enjoying this story, therefore this will be the last chapter for a while. I will browse the web for other similar stories to see how this can be improved before posting further after today.

Harry was sitting in his room, holding the small glossy black buttplug he had been "gifted" by Cho yesterday.

He had to be honest and say he was of course curious about it and how it would feel.

Like many men before him, and many that would come after, he had experimented at school with a finger while in the shower. It turned into a messy and painful attempt and he decided not to try again.

Now however, his dick was locked up and as per Cho's directions, if he wanted to get off again properly he would have to play by her rules.

And that meant inserting this tiny, little monster. 

He had returned to his room last night all locked up and leaking precum all over his panties.

After cleaning himself up in the bathroom, where he did in fact learn that standing and peeing with this particular cage would be impossible, causing him to have to sit down mid stream, and pee like a woman, just as Cho had suggested he do. That led to a quick shower, and a clean pair of thong panties, bright pink this time.

He lay in bed considering the changes he had made to himself, and trying to remember everything he had read or seen regarding butt plugs from his sneaky perusal of Seamus' porn magazines from under his mattress while at school.

He had to make sure he was as prepared as possible for his attempt, as he knew would try. Not just to avoid disappointing Cho, but future orgasms depended on the outcome. 

The one and only thing that he could remember about his past porn magazine excursions were that the people involved in anal spat alot. It didn't take much for him to realize that that was in fact for lubrication.

So he knew that, that would be key for his attempt. 

Tomorrow though. He would ensure to drink lots oforange juice for breakfast to help try and buildup enough saliva and then he would make his attempt. 

* * *

If Cho found it odd that Harry didn't dress this morning for breakfast, she didn't say anything about it.

Although, Harry coming downstairs in only a bright pink panty, (his breasts had finally fallen off during the night), was only going to end in one way, especially when she noticed the way his caged cock bulged against the front of the panty. The wet patch from his leaking dick didn't help matters.

So Harry shouldn't have been surprised when he found himself lying on his back on the dining room table, Cho kneeling over his face as she ground her leaking pussy over his mouth and nose as she rode him to one orgasm after another. She took an especial kind of joy out of the names she was calling him, now that she had him all locked up. 

Being called out as a sissy, and having a little clitty instead of a dick should not have made Harry's dick twitch as much as it did, and Cho notice every little twitch, making it a sort of game calling him different variations and trying to see what got the biggest response. 

Him grabbing her thighs, pull her down even harder to his face as he tried to eat every inch of her should have been a big clue that he particularly enjoyed being called a little, fucking girly slut. 

Her morning orgasms over, Cho tidied herself up, and left the house to continue her shopping , leaving Harry to his own devises, which suited him well.

He didn't eat any breakfast as he wasn't sure how a full tummy would effect his experimenting, so he instead just finished up washing the cum his mouth still tasted like down with some orange juice. Feeling that his mouth was adequately salivated he returned to his bathroom.

The little plug lying on the bathroom counter seemed to have grown to enormous proportions whilst he was away. Or maybe that was just his mind playing tricks on him.

He discarded his panties, and took the little plug tentatively. He rolled it between his hands, examining every inch of it, even going so far as to give a tiny lick, just to check. It of course didn't taste like much, which wasn't surprising.

He decided there wasn't much more he could do to prepare, so gave a thought to the layout of the bathroom and decided to make his attempt in the large shower, in case he made a mess. 

Mind made up he put two folded towels down to try soften the floor and knelt down on them.

He had spent some time thinking about it and came to the conclusion that the anal sex he'd see in the now 'infamous' porn mag, the women were all on their hands and knees, doggy style it was called. Whether that was in fact the best position for this or not, he didn't know, but was going to start there in his attempt.

Settling himself comfortable, his caged cock hanging between his legs, he took the plug in one hand, spat a glob of spit onto the other and started to spread it around on the toy as much as possible. He spat a few times making sure to cover it as much as possible, before reaching a hand between his legs, and feeling his tight anus with a finger, almost to check where it was. His fingers, confirming the position gave him the idea to wet that a bit too. It was as he pulled his hand back to give his fingers a lick, did he realize that his dick was pouring out precum. Precum was quite slick in his opinion, so he just swiped as much of that as he could, and reached back again, rubbing the slickness against his arsehole a bit. 

It didn't feel like much to him ,s o he kept scooping up his leaking precum and rubbing it in on and around his tight puckered up rosebud. 

Feeling adequately lubed up to give it a start, he slowly reached back between his parted legs and started to press the sharp end against his arsehole. He pressed a little harder when there was no give at all, and with no success decided to try something else. He scooped up some more precum with his finger and reached back again. As he rubbed the wetness into his tight hole, every now and then he'd press the digit a little harder, and after a few attempt, and a deep exhale, he managed to get the tip of his finger to breach his hole. That seemed to be what his body was waiting for because when he wet his finger again and pressed, it seemed to go in much easier. He also realized that exhaling deeply and slight pressing back as if trying to fart helped alot. With this new knowledge it didn't take much to get his finger in all the way into his arse. The precum helped alot and his finger easily slipped in and out, as long as he didn't squeeze his legs, which seemed to cause his hole to close again.

It didn't feel like much either. Just like he was having a particularly long poo. The finger test, didn't give him much hope that he would enjoy this at all, but he had to continue. 

After ensuring his finger could go in and out quite easily , he decided to try the plug again. He didn't want to lick his fingers, that had just been in his arse, so just raised the plug to his mouth and sucked and licked it a few times to get it wet again, and returned it to his rosebud. He rubbed the tip against his hole a few times, and then started to press in again. It seemed to go in a little but the stretching immediately cause him to tense up, which closed his hole right up again. He was definitely feeling frustrated at this point, so decided to try another position instead. He knew that if he was on his feet and squatting down he would be able to reach better, so he he stood and squatted down until his arse was just above his ankles, and leaned back slightly against the wall. 

He rubbed his dick into his leaking precum again, and easily managed to slide the finger into his hole again. This position did make reaching easier. He then rolled the plug around against the tip of his leaking cage and spread as much of the precum around it and reached back to try again. He pressed the tip of the toy against his arsehole and felt it give a little. He pressed it in, until he felt the slightest pain as his hole stretched. As soon as he felt the pain he relaxed and pulled the plug back, and on his exhale pressed it back again, and felt like it went a bit further this time. The slight pain was still there but felt a little more bearable this time. He kept that up for a few minutes, feeling like every time he pushed that the toy must be getting closer to popping in. Every time he pushed he expected the plug to pop in, and that kept him going. His hole was burning proper by now, and he was sure that it must be bright red. He just hoped he didn't tear or hurt himself. 

Eventually after feeling that the toy was so close to popping in, but not able to push any harder, he gave the toy a push on his exhale, pushing through the burn until he felt he was close, then he dropped his arse right down until the toy was against the floor. The toy jammed in his hole, his arse stretched red and painful around it and being held in by the floor, he placed his hands on either side of his feet and slowly lowered his weight down onto the toy. The burning pain was building, and as it reached the point where he had to stop and pull out, he felt it. 

It was almost as if he could hear the *pop* as the widest part of the plug finally breached him. The pain immediately disappeared, leaving only a slightly dull ache, and he expelled a deep breath he didn't know he'd been holding. The instant relief he felt was almost as good as an orgasm. 

He just sat there taking deep breaths for a minute, before deciding to try stand up. It was on shaky legs he managed to get up and noticed that although the plug wasn't that big, he could help keeping his legs slightly wider to accommodate it. He managed to slide into his panties with some difficulty, as bending down to get his feet in just caused the plug to move about. 

He couldn't say it felt amazing, but it didn't feel bad per say. Just different. He got himself dressed in a baby blue pajama pants and a white t-shirt with a unicorn on it and made his way slowly to the sitting room to wait for Cho.

As he was walking he realized something else. "FUCK!"

He would have to remove the plug to shit and put it back after. He wasn't looking forward to that.

He was however eager to show Cho that he had followed her instruction. 

It was as he sat down on the armchair that it happened.

**********

_At the same time...._

Cho was at a nearby coffee shop, having a quick cappuccino while waiting for Daphne Greengrass, her old school friend to join her. 

It was as she took a sip, that she felt her handbag vibrating. She opened it under the table, so as to hide the contents, and saw a little stone tablet with some runes, glowing a soft pink and vibrating gently. 

Giving a wide grin at that, she quickly made her way to a bathroom and closed the door. Removing the little tablet and her wand she giggled to herself and touched the wand to a specific rune on the tablet and giggled some more. She would have to leave her shopping for today and get home as soon as possible.

***********

_With Harry...._

It was as Harry sat down slowly onto the armchair to avoid jolting his sensitive arse that it happened. He had just removed the weight from his arms and settled down , when the plug in his hole started to vibrate at what could only be described as a violent manner. It was enough for Harry to give a startled jump, landing on the plug which seemed to press it even deepened. It felt like his whole body has gone into a fit. He slid right off the sofa onto the floor and tried to curl himself up through the intense vibrations that were coursing through his arse.

The feeling seemed to last for about a minute when all of a sudden he started to cum. The vibrations felt so good, his cock starting spurting cum out, soaking right through his panties and making it ;look like he peed his pants. He kept twitching as the orgasm rocked through him without stopping.

It felt like it would never end, and even when he stopped cumming, and just spurted little drops of clear liquid the vibrations continued. 

He wasnt sure how long it continued before he either zoned out completely or just passed out from the pleasure of it. 


	6. Chapter 6

**Summary for the Chapter:**

> Things start to get interesting

Cho had returned from her trip early after remotely turning the plug vibrator on, and had found Harry in just a pair of panties, lying in a puddle in front of his favorite armchair. 

After a closer inspection, she discovered most of the puddle to be from all the cum he had squirted out during his analgasm, and quite a bit of drool as well. 

He almost seemed insensate after the 20 minute long orgasm. However, Cho squatting down next to him to do her inspection seemed to bring some intelligence back into his eyes.

"Cho...*hic*..... what did you do?" He whispered out. "It started *hic* vibrating and I *hic* lost control, and I couldn't get it out *hic*."

Cho seemed to find this quite hilarious as she fell down onto her bum and started laughing uproariously. 

"I'm S-s-sorry Harry" she got out between laughs.

"I didn't expect you to get the plug in so quickly. I hadn't even given you the bottle of lube I bought yet" She giggled out with a hand in front of her mouth, trying to hide her grin. 

"I was only planning to test the plugs remote when we were together back home, but when I got the notification that you had inserted it, I couldn't help myself." She started giggling again.

"It does seem like it works though. You look like you enjoyed yourself so much, you've even given yourself hiccups" She indicated the puddles around him.

Harry just gave a groan as she tried to get himself to his wobbly feet. He didnt get far, before he realized he definitely wouldnt be able to stand. So just ended up crawling on his hands adn knees slowly towards his room.

"Just please *hic*, warn me next *hic* time." He muttered, pointedly ignoring her continuing giggles.

"Mmm, next time he says," Cho whispered to herself as she watched Harry crawling off. 

"Seems you enjoyed this way too much. Maybe its time to make some adjustments."

At that Cho removed the rune covered remote from her purse, and after glancing between the little parchment with instructions, she tapped another few runes with her wand. Giggling again when she heard the squeak coming from Harry's direction as the plug grew a little bigger in his arse. 

* * *

The week since Harry had first managed to insert his butt plug had been quite interesting for him. 

Not only did Cho change the plug size at random times of the day and night, she also played with the vibrations at the most awkward times. Falling off his sofa when Daphne was visiting Cho had been particularly embarrassing, when Cho had switched the vibration of for 1 second bursts. (Harry still dressed like a man when Daphne visited Cho.)

The smirk and twinkling eyes Daphne gave him when he just stood up and said he fell asleep, seemed to give away that she knew more then she was letting on.

Strangely, it never occurred to him to just remove the plug and leave it out. He noticed quickly that when he did remove it, he felt completely empty and had such a yearning to get it back in as soon as possible. 

He was also convinced that Cho had a alert ward on his bathroom, as whenever he went to the toilet to have a dump, the plug seemed to grow a little in the time between him removing it and re-inserting it. It always took him about 10 minutes of slow work getting it back in, and that was even with the correct lubrication now being given to him.

It was during one of his bathroom breaks that Cho had walked in on him. He had been feeling incredibly full and his boi pussy, as Cho had started calling it, had started to burn a little like it did when he was inserting his toy. He was sure that Cho had been increasing the size to bigger than before.

So he had gone to the bathroom, cast the mirror charm on the tiles, squatted over over it butt naked, and whilst keeping an eye on the toy, had slowly started to pull it out. 

Cho had felt her alert charm go off, and had gone to see what Harry had thought of her latest adjustments, silencing her feet as she went.

Harry had to keep letting go of the plug as the pulling he was doing to remove it seemed to just burn worse the never, Keeping an eye on the mirror, he could see the size of the bulb, as he was pulling and definitely wondered if he'd get the plug out at all. 

He took a deep breath, and once again started to pull on the plug with a slow, constant pressure.

After what seemed like hours, but was only in reality a minute or two, the plug burst out of his arse, causing an orgasm to burst out of his cock at the same time.

He was so surprised that he didn't manage to move his head away in time, causing more than a few spatters of cum to spray up against his hanging hair, and all over the floor.

Looking down again quickly, he noticed the size of the plug. It was easily 2 inches wide at this point. Looking a little more he noticed that his arsehole was wide open, gaping so wide he could probably put 4 fingers into it by now. Just as he open his mouth in shock, he felt his muscles clench and the gape started to close, winking open and close almost like eyes that were slowly falling asleep. 

Slowly sitting down onto his lower back to avoid sitting directly onto his arse hole he finally noticed Cho standing by the door with a wide smile on her face. Hands held up in front of her chest like a proud mother. 

"Oh Harry, you're doing so well. Your pussy is so sensitive. Even pulling out your toy makes you cum. That is so amazing!!! I can't wait to fuck that cute little arse of yours and make you cum like that" She seemed to be positively ecstatic at the changes to Harry's arsehole. 

"Oh, I didn't see you standing there. I'm not sure about that though. It is really sensitive. I even orgasmed while taking a d- uhm, poo last night" He admitted while blushing.

"I don't think being penetrated will work too well"

"Oh nonsense Harry. This is exactly what I've been training you for. To be a proper little butt slut. I did tell you that with your tiny, clitty, cock caged up, that I'd show you how to have even more amazing orgasms. Wasn't I right mmm? I do think you should be thanking me." 

Harry didn't look to sure about, and Cho easily saw the expression on his face. 

"In fact, get on your knees! You are looking much too ungrateful. Crawl over here and kiss my feet."

"NOW YOU FUCKING SISSY SLUT!!!!" Cho shouted out when Harry didn't move immediately. 

Harry gave a start at being spoken to like that, but before he could think too much about that, he fell onto his hands and knees and crawled too her as quickly as he could.

Slowly bending his arms, he gave a quick glance up and saw her expression, when he was close enough he took in the sight of her shoes. 

She was wearing a pair of her favorite black stilettos. He first gave the left one a kiss, then the right. And glanced back up to see if she was satisfied.

"Very good. But now you've gotten lipstick on them. Lick them clean, and after each lick, tell me how thankful you are for what I've helped you achieve."

Harry immediately started to lean back at that to move away, but came to an abrupt stop as Chos left leg started coming up, and came to rest on his back, the heel digging into his left shoulder painfully. 

"You are going to be punished for hesitating my little slut. But if you do not do what I have commanded you, the punishment is going to be much, much worse." With that she pressed down a little with her leg, cause the heel to dig in a bit more.

Harry flinched at the pain, and sank back down to his elbows. 

Giving a short lick to the top of her shoe, he started to offe his appreciation.

"Thank you Cho, *lick* for what *lick* I've achieved.*lick" He did the same with other shoe as she brought it back down to the floor. 

"That doesn't sound very specific or grateful Harry. I also think you should start to call me Miss Cho. Now try again!"

Harry gave a slight shiver, and started again.

"Thank you * lick* Ch-, uh, Thank you *lick* Miss Cho *lick* for allowing *lick* me to be a proper *lick* butt slut and to dress *lick* like a proper sissy *lick*."

"That is much better my little girl. You have done well. You sound very appreciative now." Cho was smiling widely at seeing Harry lick her shoes on his knees. 

She looked up and saw the reflection of herself in the bathroom mirror on the wall. She gave a little shiver of delight at seeing her standing there, Harry on his hands and knees before her. It was such a delightful image. It definitely wasn't something she had ever expected of herself. But things had just fallen into this sort of weird place. She had never considered dominating anyone, but Harry just gave off this aura of submission. She couldn't help giving into the desire to control him.

She noticed his red, puffy pussy reflecting back at her. Leaning forward, she scooped up some of the cum from the tiles and with her cum coated finger reached over and gently rubbed it into his hole. She was pleasantly surprised by how her finger seemed to sink into his pussy and just be swallowed up. She may need to move up her plans a little if he had come thus far in so short a time. 

Looking down at him still kneeling in front of her feet, ignoring her finger in his arse completely, she decided to take another step along her grand plan. 

"Harry, one last thing before I leave you to clean up." 

He seemed to sigh in relief at that

"I want you to scoop up all your cum from the floor, and your hair, and eat it. Right now."

Harry was a little surprised at first, but quickly realized he wasn't that surprised by that. He slowly leaned back so he was kneeling on his knees and scooped up the come on the mirrored floor. Slowly he reached up to his mouth. He stuck his tongue out and gave a tentative lick. It was cold already, and tasted quite salty and a little sour. Even the little lick seemed to make his mouth feel all slimy. Glancing up at Cho's stern face, he gave another lick. Realizing it tasted the same, he decided to just get it over with, so slowly put the finger in his mouth and sucked as much of the cum off as possible. He reached back down and gathered another dollop. Doing the same again. He had a bit of difficulty swallowing it though. It felt as if all the cum was just coating his mouth hand throat but not actually going down completely. When he had finished all the cum he could find he looked back up and saw Cho smiling down on him.

His heart gave a little jump at seeing her smile at him. He did love making her happy.

"Good girl. See it wasn't so bad. You might even learn to like it. I think from now on, anytime you have an orgasm, you need to eat all your yummy cum for me. Ok?" 

"Good girl." She said at Harry's slight nod as he looked down again.

* * *

Harry was in the shower the next morning thinking of all the things he'd done recently. He had never considered doing any of it before, and now that he was doing all these depraved things, he couldn't seem to think why not. He might have hesitated a lot while Cho was "training" him. But he had so far enjoyed everything she'd forced him to do. Even if he hadn't liked it all at first. He liked it all alot after that though.

He was still thinking about eating his cum the previous night when he felt a spell hit him. His arms and legs locked together instantly and he felt himself starting to fall forward. He was just starting to panic about hitting the shower wall at the end of his fall, before he felt a hand grab his shoulder, and slowly lower him down to his back. The water spraying down on his face immediately stopped and he saw Cho coming into his view. 

"Sorry about that my little Sissy." She said as she knelt down next to his head.

"I was talking with Daphne this morning and just had to tell her all about my little sissy slut I've been training. She was understandably upset at me keeping secrets from her, so I had to offer her a little something to make it up to her."

Harry eyes went wide at hearing that. He knew that Cho had been keeping his feminization a secret from everyone so far. 

"Oh dont worry. It's nothing too bad, i assure you. She did tell me her idea, and I have to admit it does seem quite interesting." Cho looked behind her and gave a little wave with her hand

"Come along Daph... You've of course met Harry before, but now I'd like to introduce you to my little butt slut." 

Harry started panicking and trying to break through the body bind, and gave a slump of defeat as he saw face of Daphne Greengrass coming into view. 

"Hello Potter." He could practically hear the smirk in her voice. "If I knew you were such a little slut I might have claimed you in school already. And you have such a feminine body."

She was grinning as she examined his body slowly from head to toe, 

"Ooooh you have such a cute little clitty cock. Does it do any trick?" She started laughing loudly as Cho gave a startled giggle at that. 

The two woman in his view glanced at each other and grinned wider.

"So I'm sure you're wondering what I've been promised. Well you won't need to wonder for too long." Daphne said, as she slowly lifted her tight dress up her legs and stepped over him so she was straddling his face, and looking down into his eyes. 

Harry couldn't help glancing from her eyes, down so he could see up her now raised dress. He noticed straight away that she wasn't wearing any underwear. It was only as she bent her knees slightly so she was could lean down slightly that he noticed the small jewel between her tight arse. 

"From now on, you will do what ever Daphne tells you, do you understand my little slut!" Harry quickly glanced to Cho's face, and then back to Daphne's. 

It wasn't like he could do anything else at the moment, being in a body bind as he was. Daphne seemed to read the thoughts on his face, as she drew her wand from- somewhere- and waved it in a little circle over his face, _"finite_ ". 

he felt his head fall sideways slightly, and realized she had free'd his head from the bind. 

"As you wish Miss Cho. What she going to do to me?" Harry asked as he turned his head to look at Cho.

"Oh don't worry yourself little girl. She has some amazing ideas for you." 

That didn't reassure Harry at all.

Daphne gave a giggle at the concern on his face.

"Oh, don't worry so. I have a lot of experience with little sissies. My sister and I have spent years training up little Didi up. You'll probably remember him as Draco though." She laughed outright at the shock on Harry's face. 

"Oh don't look so surprised. My sister was forced to marry him, but he was honestly no good as a husband.... or a man really. It didn't take much to get him all sissied up. He is very entertaining now. Maybe I'll tell you of some of the fun things he does for the men Astoria and I bring home." She smirked evilly at him as he felt the distinct urge to run far, far away.

"I do have to admit though, as good of a sissy slut as what he is, I have never seen a more useless dick than his little clit, until now." 

Harry turned red in humiliation, and blushed even harder when his dick twitched at that.

"So now, Miss Cho has offered me a favor in apology for keeping this juicy little secret from me. I hope you enjoy this as much as I will."

She gave Cho a grin, then slowly started to lift her dress up to her waist completely, freeing up her legs as she started to squat down over him.

Harry immediately thought that he would have to eat her out, and he had to admit that she had the sexiest pussy he'd ever seen. 

He gave his lips a little lick in anticipation. He would only admit to himself that he really loved licking Cho's pussy, and this didn't seem like a punishment at all.

He gave a blink as Daphne stopped lowering herself when she just inches above his mouth. She smirked a little at Harry's confusion.

"Oh, you thought you were going to be licking my pussy" Oh no. Nothing like that little sissy. At least not yet." She giggled at that.

Harry glanced between her face, and Cho's and then back to her pussy that was so close to his face, just out of reach of his tongue. 

He saw a twitch just below her pussy and saw the emerald green jewel of the plug move, as she pressed out a little. It looked like she was trying to expel the plug with just her sphincter muscles. She reached a hand down and with two fingers, slowly spread her two thin pussy lips apart, exposing her vagina and clit. As he examined her open vagina in minute detail, noticed the little slit above her vagina starting to open. Before his brain could make the connection he jerked his head as a drop of golden liquid fell out onto his cheek.

"Here it comes little slut. My golden nectar, and you had better swallow it all. If you get my shoes wet, you will be punished," 

That was all the warning he got as the little drop of golden liquid turned into a torrent of hot urine spraying out quite violently against his face. He started to turn his head sideways, when he felts something hard and flat starting to press down on his balls that were on the floor between his legs. 

"Drink it slut, or I will crush your little marbles!!" Cho didn't seem to be teasing him now, as she kept her shoe against his ball sack.

Harry turned his head back up, and opened his mouth. The golden urine started to fill his mouth at a rapid rate. He knew it would start pouring right out at any moment so gave a large gulp. It filled up again almost as quickly again, so he swallowed again, and again. He had to admit that after the first taste, it didn't taste as bad as he expected. He didn't enjoy it by any means, and the heat of it was very odd, but he didn't feel the urge to throw up either, so that was at least something. After about a minute the stream started to taper off completely and as it slowed down to a few drops, Daphne lowered herself completely against his mouth.

"Go ahead slut. clean me up properly."

Knowing it couldn't be as bad as actually being used as a toilet Harry stuck his tongue out and started licking her as clean as he could.

"Uhhh, that feels much better . Thank you Potter. I was waiting all day for that. I feel much better. Maybe we'll do this again." 

She stood up, stepped back over him and started leaving the bathroom. 

"I forgive you now Cho." Daphne smirked as she left. "I'll wait for you in the sitting room." and she left without another word to Harry.

Cho removed her foot from Harry's balls after a slight little twist of her foot. 

"You did a good job my little slut. Or maybe I should call you a toilet now?" She laughed at his face.

"Don't worry though, I don't feel the urge to use you as a toilet myself. I'll leave that to Daph. Now, finish cleaning yourself up. I want you to dress up in something sexy, makeup, the works. I want to show you off to Daphne properly so she can see how good a girl you are."

She patted Harry's cheek, stood up and left. She was almost out the door as she waved her wand over her shoulder, _"Finite incantatum"_

Harry felt the spell lift and his body relaxed onto the shower floor. 


	7. Chapter 7

The same night that Harry had been pissed all over by Daphne, he had dressed up as sexily as he could. He had put on a pair of red, crotch-less, tangas, and a black lace see-through baby doll. His locked cage bulging in the panty and his butt plug showing through the missing section of panty. He had done up his eyes in a dark, wide eyed innocent style and made his lips red and plump looking. He slowly walked down the stairs in his stiletto heels, and found Cho and Daphne sitting in the living room, drinking large glasses of wine. 

He then proceeded to spend the night on his knees licking and eating them to numerous orgasms as they kept chatting to each other and only stopping to call him a dirty slut or demean his tiny leaking cock. Even once having to swallow Daphne's piss again. 

He found himself waking up on the floor of the living room, his face and chest hard with dried cum and piss, and the taste of his own cum still lingering in his mouth. 

It was after having a shower and dressing that he found himself having an odd conversation with Cho. 

* * *

"So, its been a while since I started working here for you, and I know this is probably not what you had envisioned when you posted your advert, I wanted to have a serious discussion on this all to confirm we are on the same page." 

Harry snorted at that.

"I don't think anyone could have envisioned things turning out this way. Not that I'm unhappy. Well with some of it at least."

Cho smiled at that. "Well that's why i wanted to chat. To get us on the same page as it were. Firstly, do you see yourself as a woman? Is that something you desire? A vagina, real boobs, etc?"

Harry gave a start at that. "Well, I have considered it and I did love having boobs, I dont feel like I would want to go all the way. I like the way things are now. I think my main enjoyment at wearing the clothes and makeup etc, is that it makes you happy. And that makes me happy. I have to admit the looks I get in public are also nice." He added the last bit slyly.

Cho couldn't help laughing at that. "You should see the looks you get behind your back."

"Ok, so that clears up that point. So of the things we'e done, can you tell me which you've enjoyed, and which you'd rather not do again?"

Harry blushed at that, but started to give it some thought. 

"Well. I have read some of the porn magazines you've bought for me and gotten some ideas of the various things we can still try and I haven't seen anything that I do't think I'd be willing to at least try once. I don't know if I will ever enjoy the taste of piss, but I didn't hate the actual experience."

Cho blushed and giggled simultaneously at that. "I don't know myself if I would enjoying doing that to you so we'll feel that one out slowly. And if you are on board with trying most things once, then I'm happy. I have a few great ideas for the future."

And that was the end of that as Cho stood up and left the room, stopping at the door.

"Oh, and if you are serious about real boobs, then I may have found someone who could help with that. Let me know if you're keen."

* * *

That was how Harry found himself in a small clinic in Paris. The nurse and the Dr didn't say a word about the fact that he was a male. Although, he did think he noticed the nurse winking at the giggling Cho when they were looking at various "models" of boobs that he could choose from. 

The clinic was a rare find, where magical and non-magical people could come for permanent body modifications. Even though the muggles only knew it as plastic surgery, the magical side of things included estrogen focusing potions, some magic and a cream, that would give you your selected modification quickly and easily. That was how Harry found himself sporting a pair of 32D boobs, with large thick nipples that. The best part was that they were completely real as if he had been born a woman. He did have to put up with Cho's comments about his slutty whore side coming out when he found out he was much larger then Cho's small hand fulls. 

He celebrated by visiting Bev again, and getting himself a whole new selection of matching bras and panties.

* * *

He had just had a long bath where he played with his boobs and nipples for more then an hour. It was as he stepped out of the bathroom that he realized Cho was waiting for him on the bed. 

"I have a surprise for you. Well two actually. They are something that will help you in the future when we play." Cho said as she pushed the narrow box on the bed closer to the edge. 

Harry was surprised at the gift, more for the fact that it wasn't the usual gift of underwear. It didn't take him long to consider what they might be as he slowly started to unwrap the box. 

As he got the box open, he realized he was half right. It was indeed a sex toy. However just what type it was is what caught him off guard. There were two similar looking silicon dildos lying on a bed of purple paper. the one was slightly thicker then the other at around 1.8 inches thick, and the other was about 1.4 inches thick. the thinner one was slightly longer at around 10 inches long, and the thicker one was about 7 inches long. They were a tan color, very similar to Cho's oriental coloring. They were covered in veins and ridges and looked incredibly realistic, and had real looking ball sacks hanging on the end. He slowly touched the rubber with a finger and realized it felt exactly like real skin too. the balls were loose and wobbled around in the sack. 

He admired them and knew that this was where his arse training was heading. Although something confused him. 

"These look amazing. But why are there two Miss Cho?" He asked as he glanced back up.

Cho seemed to be waiting for this exactly as she grinned and stood up from the bed. Taking the two dildos gently, she walked to the nearest wall. 

"These are obviously magical dildos from my new favorite store. There are a few features. But most importantly, they are trainers. And always work together."

She then promptly, pressed the longer one against the wall at about knee height and tapped it with he wand, causing it to stick there. She then pressed the other on the floor between her feet, facing up and tapped it too. 

It didn't take Harry long to put the clues together and give a step back in nervousness. He had obviously been considering the idea of sucking Cho's strap-on before she fucks him with it, but this was making that dream a little more real. He shook himself as he paid attention to Cho. 

"So this is a sissy trainer for little sluts like you." She grinned at him.

"There is one dick for you to suck and one for you to fuck... At the same time... and at the end of each practice session you will get a print out that will rate your skills. If you manage to get above a predetermined score, you may be made to cum by the toys. They also contain a 'filling' as it were provided by the store, so don't be surprised if you get a spray down you're throat or up your little pussy hole. The best part, is that when you get skilled enough then the dicks will start moving too. fucking you as it were... So get your fucking hole onto this dick right now!"

That last comment caught Harry by surprise but got him moving quickly. He didn't know if he was nervous or excited or a combination. He knew that the plug in his arse had been grown to thicker then the dick he was currently lubing up, but the plug in his arse, grew whilst in him. It didn't move in and out continuously. 

Once lubed up enough he glanced at Cho who was squatting down nearby, her short skirt wide open, showing her uncovered pussy in all its glory. He glanced up and caught her sparkling eyes. The look gave him a shiver, so he slowly looked away, feeling a little ashamed suddenly. He was about to fuck and suck fake dicks in front of a woman that refused to even touch his own cock. 

He dropped the towel he was wearing and slowly lowered to his knees, leaning forward and reaching behind him. As he grabbed the plug, he gave a long deep breath out, and on the exhale started to pull the plug out. It didn't take much before it popped out leaving him feeling the inevitable emptiness that followed. 

He rose back to his feet and moved so he was squatting over the slicked up dick standing up on the floor, the tip was just teasing the already closed hole. He looked back up to Cho, and keeping her eyes on his, he slowly started to lower himself. He didn't quite manage the tip of the dick in his hole, before he needed to reach behind him and pull his arse cheeks apart. With a deep breath he resumed the lowering until he felt first the usual burst of pain as his ring stretched around the dickhead. With a little jolt, he managed to pop the head in causing him to sigh in both relief and an immediate pleasure. After getting the head in a little more he had to start to get his knees under him so he was kneeling with the dick pushing deeper as he settled. It was as he got on his knees and arched his feet to sit on his knees and the balls of his feet that he felt the dick touch a sport inside him. The orgasm hit him completely by surprise, and he was just as surprised when the cum spurted with a force out of his cock, instead of the little dribbling it had been doing lately. 

"Oh my. You really do have a sensitive little pussy. cumming like a whore from the penetration alone. We might need to hire that little cock hole out if it performs like that." Cho said with a large grin on her surprised face. 

Harry felt like he couldn't be more embarrassed. He had never cum that quickly before, not even from Cho fondling his hole and cock cage. He was jerked out of his closed eyed, embarrassment. 

"That other dick isn't going to suck itself whore. Get working."

Harry slowly opened his eyes and looked at first Cho's smirking face, and then turned to take in the dick in front of him. It looked much larger from this position. He nervously bent forward a little, and realized he would need to actually kneel up more to reach the cock in front of him. Kneeling forward a bit he felt the dick stretching his arsehole shifting out a bit. 

With his tongue licking his lips, he slowly gave the dick in front of him a quick lick. It didn't taste rubbery like he expected. It tasted a bit odd actually. He gave another slightly longer lick. Then another, and by the fourth much longer lick he started to realize what it tasted like. It was a bit tangy, and musty and almost tasted a bit sweaty. With a little start he turned to face Cho again surprise on his face. The start caused the dick in his arse to press against his prostate again causing more cum to shoot from his dick. 

Cho just giggled at his surprised face, "Yes it is supposed to taste exactly like a real dick. I was quite impressed myself."

That question answered, Harry turned back to the fake cock in front of him. If he was to practice, why not go as real as possible then. Made sense. 

He started to lick again. Never having seen or been given a proper blowjob himself, he had no idea if he was doing it right, but judging by the pictures he had seen in the aforementioned porn magazines, he knew he would at some point need to get much more of the dick in his mouth. Or that's what the images looked like. So after some more licking and a few kisses, he slowly let the dick head enter past his lips, all the while he kept licking what he could of the dick that was inside his mouth. His eyes briefly went the side, just barely catching Cho's face in the corner of his vision. 

"Keep going cock sucker. You have a lot of meat to go." She said as she kept watch. 

He couldn't help but notice that she kept licking her lips and it looked like she very much wanted to start to finger her now dripping pussy.

He looked back and realized that he would need to move to get the dick in further, so slowly leaned forward letting the dick in his arse start to glide back out as the dick in his mouth went a little deeper. Sooner then he expected hie felt the dick against the back of his tongue, causing him to feel his gag reflex act a bit. He immediately pulled back, rocking into the dick in his arse again. He started to just do slow small rocks forward and back. Just far enough for the dick to pull from the back of his throat to his lips and back again. He kept it up feeling the dick stretching his arse on each rock, not going far enough down to touch his prostate again, but it still felt suspiciously good.

After a few minutes he noticed that Cho had given in, and was sitting wide legged on the floor watching his be fucked from both ends as she shoved two fingers into her drooling cunt.

He was caught off guard at that.He had never actually seen Cho finger herself before. He had always done it for her. He was so aroused by the sight, and realized she was aroused by what he was doing so decided to do as well as he could. 

He lifted his hands and with one hand reached back and pulled one arse cheek apart and started to gently pulling and roll the balls of the dick in front of him with his hands as he started to rock a little harder. It was by the third rock forward that he accidentally swallowed some built up saliva in his mouth at the same time as the dick hit his throat and it just went a little further. It caught his unprepared enough that he almost fell off the dick completely. With a glance to the furiously masturbating Cho, he tried again, leaning forward and swallowing as the dick entered his throat and press. It started to go down his throat and it hurt and felt like he was going to cough or choke or pass out but he also felt a sense of accomplishment.

He kept pressing as it went deeper and out, and deeper and out until he went forward, feeling the cock press all the way down his throat and his nose bumped against the wall. 

The pride he felt was mirrored in the expression in Cho's eyes when he glanced at her again. 

Managing to get the dick down his throat he, started to rock back and forwards, getting the dick all the way down his throat and then rocking back until the cock in his arse hit his prostate. He kept up the rhythm, feeling another orgasm building before being surprised by what felt like a slight thickening of the cock in his mouth when he all of a sudden felt it start to spray a large amount of liquid down his throat. He immediately started to pull back and had half the dick out his mouth when he realized what he was tasting. The cum was hot and salty and tangy and already felt like his throat was coated thick. He tried swallowing as much as possibly while trying to decided if the cum was also artificial or was real that Cho got from somewhere. It was as he swallowed what felt like the last bit that he felt the dick in his arse also swelling before a huge burst of cum shot out into his inner bowels. It felt like his colon was stretching to unheard of proportions as it kept spurting and spurting which led to Harry's little dick spraying out another orgasm as well. It was as the last spurt died down in his no longer virgin hole, that he fell forward, the cock sliding out his arse, and a large amount of cum along with it. He fell down on his side and pulled his legs up a little . 

Cho seemed to have finished what she was doing too as he felt her press the plug back into his still gaping hole. 

"Lets keep some of this nice cum for later shall we." She said as she picked up the print out that had fallen on the floor along side the dick.

"Lets see how my little sissy whore did then. Mmmm..." She said as she browsed down the page. 

"According to this, I was inaccurate about you being a total amateur. You're cock sucking skills need some work, however you're deep throat skills are at 'Gloryhole' level."

She burst out laughing.

"You are such a natural. I might have to really consider renting out you're holes."

"Your arse hole seems to be naturally sensitive and a superior fuckhole. Mmm, seems that next time you use the trainer, you're pussy hole will get some advanced training. However your moth needs some actual sucking work."

"Such a good little slut." Cho said at the still dazed Harry lying in a puddle of cum. 

Cho Scooped some of the spillage from his arse hole onto a finger and lifted it to Harry's mouth, giggling as he obediently opened his mouth hand sucked it off. Blushing red at what he had just done.

**Notes for the Chapter:**

> Quick poll. Would anyone be interested in seeing any images of the clothes, toys and possibly scenes as they read the story


	8. Chapter 8

**Summary for the Chapter:**

> Date night commences

Last night, Daphne had entered his room so she could greet him with her, by now, usual mouth full of piss, only to come to a stop, causing Cho to walk right into her. There was Harry, bent over in the shower, one dildo stuck to the wall behind him and one stuck in front of him. He was bent over and rocketing himself forward and back into the two dildos. One going down his throat and the other into his arsehole. He was going at it with such obscene moans coming from his mouth as his little dick dripping out a stream of cum, that he hadn't even noticed the two woman when they entered. He had noticed previously, that the harder and more enthusiastic he rode the dildo in his arse, the greater and longer his orgasms were. Therefore he seemed to find himself playing with his two cocks multiple times a day, and being caught at that moment, turned into a 6 hour session, where spent the night fucking and sucking his cocks, while Daphne and Cho critiqued and humiliated him. He then spent some time sucking out the woman, and even watched Cho and Daphne themselves fuck the two dildos while he watched, as his little dick wasn't good enough for proper sex with a woman.

He still hadn't progressed all that far with his cock sucking skills yet. Like Cho had said, he found himself to be a natural at deepthroating, and he absolutely adored the cum that was coming out of it, not even bothered by the fact that Cho was refilling the dildos up with a spell and liquid from a bottle she brought from the store. He was certain it was real cum but hadn't gotten Cho to Admit it yet. He also couldn't fathom where she would be getting a liter of fresh, thick, cum every day. But he didn't get great reports on his actually oral skills when he wasn't deepthroating. He had more then one passing thought that it might be easier to practice on a real cock where he could receive live instruction as he went.

He of course kept those thoughts far away from Cho.

* * *

So he woke up late the following morning. His boi-pussy was absolutely ruined. He felt tender and sensitive, and it was only while lying in bed and casting a healing spell on his hole that he finally felt some relief. Slowly he felt the muscle repair itself and start to finally close.

He sat up gently and noticed the note next to his bed. 

**_Harry,_ **

**_I think by now that I deserve a proper date._ **

**_I would like for you to get yourself ready_ **

**_and looking as sexy as you can, and I will_ **

**_meet you tonight at the house at 8pm._ **

**_Don't be late._ **

That was quiet an exciting idea as far as Harry was concerned. He also had alot to do in order to get ready, so got himself out of bed and into the shower. He managed to get himself clean without giving into the desire to suck off the dildo again. His throat was also still a little tender from the night before too.

He got himself dressed and made after a quick breakfast, went to his favorite mall for a new outfit. After an hour of browsing he got himself a black, sheer, crotch-less, lace thong. A matching garter belt and bra. He spent alot of time deciding on clothes though and ended up getting a black, pleated wrap skirt that ended above the knee, but seemed to get smaller the more he bent forward. And a white blouse, that was just thick enough to just barely show his black bra through. He got gloss black stilettos which he spent alot of his browsing around the store, wearing for practice.

After getting his clothing sorted, he got a walk in appointment at his favorite beauty parlor (Money opened many doors) . Magic could do alot of things, but sometimes muggle was still best. 

He got himself a full body wax and massage. Got his hair refreshed and just for something new had a dark red highlight added into his normal long black hair. His hair was then straightened out and he had a dark red french mani and pedi done. One last stop was to get his makeup done by a professional. He still did his own makeup at home, but he still had alot to learn. 

Once he was sorted he returned home. He still had a few hours to go so spent that time nervously pacing and waiting. Just before 8pm, he cast a few refreshing charms on himself. Sprayed a little perfume. Ensured his plug was situated firmly and his dick was dry of the continuous precum. He then got dressed and went downstairs to wait.

* * *

Cho was about 45 minutes late, when he finally heard her coming up to the front door. 

Immediately getting to his feet and standing near the door, hoping to surprise her with his effort. As the door opened he heard Cho talking to someone. That was odd, he thought it would be only the two of them. Oh well, maybe its Daphne?

He was quite surprised then as Cho entered the house and right behind her was a large African man, who at first almost looked like Kingsley, but at second glance this man was much more muscular. His shock at the man entering with Cho was interrupted as he heard her talking.

"Oh here is my little sissy slut, waiting obediently for his Mistress. Oh, but don't you look absolutely perfect. Didn't I tell you Charles, he's such a sexy little sissy. Just like I said."

"Oh, you were definitely right, he is beautiful. Are you sure he's really a man though. I would never have guessed." Charles voice seemed to sound like he was rumbling through a mouth full of gravel. It also got Harry's brain jump started enough to start to realize what was happening here.

"Cho, I'm sorry, but I'm confused." 

"What about Harry?" Cho asked as she glanced at him, eyeing him up and down again. Before seeming to piece together what he must have thought.

"Oh wait, you thought I wanted to go on a date with you Harry?" And she started to laugh uproariously, at the same time that Charles seemed to find the humor. 

"This little slut thought you would want to go out with a little girl like him. He must be losing his mind as his boobs grows larger"

"No, no, no my little sissy. I didn't want to go on a date with you. I just wanted you to be here for the entertainment. I thought it would be educational for you to see how a real man fucks a woman." 

Harry's heart dropped at that. He had definitely started to develop feelings for Cho and had hoped that she had too. But this being "allowed" to watch another man fuck her was possibly a step to far. But just looking at Cho he knew that he wouldn't have much choice in the matter. 

He glanced down at this realization.

"Yes, Miss Cho."

That was how he suddenly found himself sitting on a chair right at the foot of the bed as Cho and Charles seemed to be devouring each other with their mouths. He was so large, he made Cho seem small and fragile. His hands were groping and squeezing and there was an occasional slap on her arse when he could manage that just made Cho squeal and grind against him all the harder. They slowly tore each others clothes off, completely ignoring Harry as he sat right next to the bed and watched. Harry was ashamed to admit that his cock was absolutely dripping precum through his lace panties and leaving a puddle between his legs. 

He got an even larger shock when Charles lost his boxer shorts and seemed to be sporting an impossibly large, thick cock that still wasn't all the way hard yet. It had to be 12 inches long and 4 inches wide with thick veins coursing all the way up, and the dick head seemed even thicker. There was no way that was going to fit in Cho's pussy. However Cho didn't seem to consider it too big herself. She immediately started to lick the large head with her tongue, she was licking and swirling her tongue around the cock head, whilst her left hand was rolling and squeezing his balls, and her right was squeezing her nipples. Charles himself seemed to just sit back on his knees as Cho went to work. He alternated by rubbing her head almost as if patting her, and smirking at Harry sitting next to them. It was a few minutes later that Cho started to actually suck his cock in earnest. She spent alot of time with the head in her mouth, but didn't seem to be able or willing to get much further then that. Neither of them seemed to mind though, as after a few minutes of that, he seemed to grab her head and hold his head in her mouth, as deep as she would allow, before he started to groan and cum in her mouth. It seemed to be alot of cum though as her cheeks had bulged out before she realized that he wasn't going to release her, and she started to swallow. 

She kept swallowing until he pulled his cock out and took a deep breath. 

"Sorry about that Charles, I'm no that great at deepthroating. Maybe I'll let Harry give your monster a go after you'd made me cum." She said with a wink as she wiped some cum off her lips. 

Harry couldn't help the nervous fluttering at the grin Charles directed his way at that comment. 

Charles just gave Cho a smile and lay himself down on his back.

"Well, come on then. Get your orgasms here then."

That was all Cho needed as she crawled up his body and stopped when his dick was right against her pussy. She reached back and adjusted position slightly, and when she was ready, she started to slowly lower herself. She hadn't go very deep before she had to lean back and use a hand to try pull her pussy lips open slightly. She also glanced at Harry and noticed how he was leaning forward, his head mere inches away from the mammoth cock that was stretching her open. 

She got the cock head in, and knowing this was the largest cock she had ever had, she pulled back and started again. She kept it up, just the head going in and out while she tried to allow her pussy to accommodate the cock. Charles it seemed was getting bored though. 

"Fuck this, We'll do it my way." And he grabbed her hip, and pulled as he rolled until he was on top, her legs stretched wide to the sides the make space for his wide hips. He grabbed her ankles and pushed her knees closer to her chest, and then without letting his cock head once fall from her vagina, he started to press into her. His grunts at her tight pussy were only met by her load moans as his cock slowly stretched her wide open as it went in. Once he bottomed out he stopped long enough to grin at Harry.

"This is what a real mans cock does to a woman, little sissy."

And then he started to pull out and ram back into her with a thunderous pace. Each time his balls slapped against Cho's arse as he bottomed out, she gave a very sexy squeak, and by the fifth thrust she started to cum as she whimpered and squeaked through her orgasm. Charles just kept going on and on.

Harry was sitting on his chair, his face close enough to get hit by some of the cum and wetness that was flinging off the two. He was so incredibly hard and horny watching Cho's pussy red and stretched around the edges. 

Charles gave a loud grunt then and started to pound Cho with a few bruising thrusts as he came in a loud groan. 

He started to slow, and eventually was getting ready to pull out, when Cho grabbed his hand to get his attention. 

She was a little incoherent, but got enough out.

"W-wa-ait.... *pant*pant*, H-h-arry, when *pant* Charles p-pulls out, *pant*pant*I want you *pant* to suck his cum out of *pant* my p-pussy. Every drop."

Harry wasn't expecting that. But decided that if he had been drinking cum from the dildos like he thought, then this was pretty much the same thing. He slowly started to move on top the bed and as close as he could get to Cho's pussy with Charles kneeling between her legs. 

Once he was close enough, Charles quickly pulled his cock out and moved aside, all the while holding Cho's legs against her chest. Her pussy was red rimmed and gaping large enough that Harry thought he could probably put four fingers inside her with no difficulty. He knelt between her legs and slowly started to lick her tender pussy. He first just licked around her open pussy lips, and immediately started to taste some of the cum. It wasn't like the dildo cum, this was hot, salty and quite bitter, but still he continued. He licked around and accidentally brushed her swollen clit causing Cho to squeeze her legs closed on his head, keeping him in place. She grabbed hold of his long hair, and he stopped licking to give her a moment to settle. His head being trapped as it was, he lost sight of Charles, but very quickly realized where he was, as the bed dipped behind him, as Charles settled behind Harry. Harry jolted forward against Cho's pussy slightly causing her to whimper, when he suddenly felt the back of his skirt flip up onto his back, exposing his hole to Charles gaze, thought the crotch-less panties he was wearing.

"So this is the famous fuck hole Cho has been telling me about. I've been wanting to find an ass that could take my cock for a long time, and this seems like it is just right."

Harry immediately started to panic and try get free, but Cho seemed to like the idea as much as Charles, and she just squeezed her legs tighter and pulled his hair harder keeping his mouth firmly pressed against her gaping pussy. And that made Harry realize that his arse would be gaping just like this pussy in a very short time. He knew as much as he had practiced though, that cock would not fit in his arse.

He kept licking the dollops of cum that started to come pour out of Cho's pussy. He could feel her clench and release her thighs as she tried to squeeze her inner walls. The cum came out dollop by dollop and Harry just kept licking it up and scooping dollops wit his tongue, and the humiliation hit him, as he realized he was eating another mans cum, from the girl he thought he was in love with' pussy.

He suddenly felt Charles part Harry's arse cheeks exposing the black jewel of his butt plug. 

With a bit of a laugh, and comment at Harry getting himself all prepared for him, Charles took the plug, and with one sharp tug, pulled it out. The pain from the sudden stretch of his anus caused Harry to moan loudly into Cho's pussy.

He felt something wet hit above his hole, and felt Charles start to rub it into and around his own slightly gaping hole. 

"A little sissy like you doesn't need any lube, yeah, so Cho's pussy juice and my cum should be enough lube don't you think."

He didn't give Harry a chance to respond as he started prodding Harry's rapidly closing hole with his monster cock. He gave a few tentative prods and realizing the hold wasn't going to magically open for him, Charles gave a hard rock forward causing his mushroom tip to press then pop suddenly right into Harry hole. The intrusion causing Harry to buck forward hard against Cho, and his nose squashed against her clit, causing Cho to scream as another orgasm rocked through her from the licking. Her orgasm seemed to help a whole new amount of Charles cum to find its way out of her tight pussy and into his mouth. 

Charles seemed to take a minute to settle, before pulling his head right back out of Harry's hole, and then rapidly pushing it back in. He did this a few times, each one causing Harry to moan in pain. He could feel his hole stretching, and burning and he was sure he wouldn't ever be able to get it closed again. By the time Harry gave in and realized this was happening no matter what, Charles seemed to be done playing. With his cock head now resting in Harry's boi-pussy, he took a breath, slapped Harry's arse hard, and shoved his cock in as far as he could go. The searing pain felt like Harry was being torn in two. He screamed into Cho's pussy, causing her to squeeze her legs and shiver through another small orgasm. Harry felt as if he would never be able to close his legs properly again. 

Charles seemed to love the tightness though as he started sawing his cock out, and back in, only managing half his length, but he was determined to get it all in. Slowly on each thrust he felt himself go deeper, inch by inch. until his balls hit Harry's small dangling balls. 

"There we go little slut. You are finally a real woman. I have my cock, balls deep and you are taking it without any complaint. You are just a perfect little fuck hole."

He gave another slap and then start to fuck Harry in earnest. He was pumping into Harry so hard and fast that Cho ended up having to let go of his head in case she hurt him. Harry ended up laying on top of Cho, his head on her breasts, as he just hugged her hard, to try keep himself still. He also started to forget about the burn in his arsehole as his prostate started feeling the cock rubbing past it on every stroke. Harry felt the orgasm building up and was mewling and whimpering and all to soon found himself arch his back so his arse had a better angle, and he was begging Charles to fuck him. 

Cho was right there with him.

"Look at you sissy, getting you're pussy pounded by a real man. You're a real fucking slut now. There's no going back from this. No toys will satisfy your'e hungry hole. Maybe I won't need to sell you're holes, maybe you'll offer them for free you fucking whore."

Harry felt the orgasm build and then he was cumming. The orgasm tore through him and seemed unending. It just kept going and going. He couldn't think anymore. He couldn't speak. There was drool falling out his mouth all over Cho's breasts as Charles kept pounding away, and then he was cumming too. Harry felt the cum moving through the thick behemoth cock and then felt it spray inside him. and again, and again and after what felt like minutes of cumming. Charles pulled his cock out, and Harry dropped down bonelessly against Cho. She just shrugged him off though, and he lay on his side, knees to his chest and kept murmuring to himself. Cho leaned closer to make out what he was saying.

"I'm a cock hungry sissy, slut. I'm a real woman now. I love cock. I'm a whore."

That was enough to cause Cho to start giggling. She looked up and noticed Charles was busy getting dressed.

"Going already? I thought you were going to stay the night?"

"Nah, I've had my fun. You did well for a petite little Asian. Maybe I'll see you again." He finished getting dressed, and leaned over to Harry.

"Thank you whore. It was fun." and slipped something into Harry's still gaping hole. 

AS he left the room, Cho leaned over the un-moving Harry, and found what Charles had left. There sticking out Harry's ruined whole was a 20 pound note. 

Payment for services rendered.

She started giggling again as she tried to sit in a comfortable position.


End file.
